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  Hey, was in Korea last year so didn't get a chance to ask you any trip questions, but this year I'm planning another trip back to Europe.

  So I was thinking of going from Chișinău to Odessa to Kyiv for my 2 week trip.

I know there are buses from Chișinău via Palanca or Tudora to Odessa (http://terra.md/ro/timetable/gara_nord/default.aspx), but wasn't sure about the reverse route from Odessa to Chișinău via Palanca or Tudora.  Main reason is I want to avoid the train since it goes through Transnistria and though I have heard it's now easier to go through (no longer needed to get off the train and go to the police station), I still feel that bribery or harassment still happens at the border when going through the zone.
  Also I'm only seeing buses leaving later in the day from Chișinău, is there any options of going to Odessa earlier? 

  Next Question is from Odessa to Kyiv.  Since it's a fairly long trip, I was thinking the train, though I believe it goes out of the way via Vinnytsia while the bus goes via Uman'.  Do they have night trains from Odessa to Kyiv with sleeper cars at all or would it make sense to just take a train to Vinnytsia, stay a night or two and then go to Kyiv?  Or would the bus be better taking an early morning bus to Uman' staying the night or two and then on?

I'm trying to go from Chișinău - Odessa -Kyiv, but may end up doing it in the reverse order depending on flights so this is why I was asking about the reverse route from Odessa to Chișinău.

  Thanks, you've always been a great help on my trips...

Obviously buses go back the same way as went here. Anyway the majority of buses between Odessa and Chișinău operate via Tudora/Palanca.

Also I'm only seeing buses leaving later in the day from Chișinău, is there any options of going to Odessa earlier?

in Winter situation with buses Odessa - Chisinau is very specific.
Thing is the road M15 (the road from Odessa - Palanca - Reni) tend to be closed sometimes (from 1 to few times per Winter, typically for short periods, with duration about 1-3 days) on Winter due to weather conditions.
For example last time it was closed only 2 weeks ago because of huge snowalls for untypically long period from ~8 to 12 Jan 2017.
During those days most of buses Odessa - Chișinău (and back) was simply canceled, the few operating ones - operated with giant detour via Bilhorod-Dnistrovsky and horribly increased travel time.
Also demand among the passengers on this route dramatically decrease for Winter on this direction. The demand drops much more significantly especially after the incidents as I've described you. People who suffered during such situation return to homes and tell everybody how horrible it was, those who planned to travel  - afraid situation will re-appear and ruin their plans, so prefer not even dare to travel. Most of them prefer postpone such travel for Spring if it's possible.

For example since 12 Jan 2017 road M-15 is completely opened, but the evidences of those, who sucked on 8-12 Jan caused dramatical drop of demand, which is already low due to the fact that the Winter. As result - after 12 Jan half of scheduled buses from Odessa to Chisinau are temporary canceled because too few travelers.
So I'm not sure if there is bus in morning, but definitely emotions subside in few weeks thus demand will restore to it's normal Winter value, then Spring will come and there will be lots of buses in each time of day.

hough I believe it goes out of the way via Vinnytsia while the bus goes via Uman'

Yes. There are few departures per day of the fastest buses (providing travel time in fact only about ~5-5,5 hours). Their scheduled travel time is 6,5 hours, but they overspeed little bit and come 1-1,5 hours before timetables. It's the buses of Autolux
http://autolux.ua/en/buy_tickets/
not all buses of Autolux are so fast, only those, which are marked as VIP (And they are more pricey). "VIP" departures of Autolux don't stop in Uman.
For example I often return from Odessa to my home city (Kyiv) by the 18:35 bus, and despite sheduler arrival time 0:40 - I always came to Kyiv before midnight (and thus I always managed to catch metro before it closes, metro in Kyiv close in midnight).Please note, despite they are horribly expensive in Ukrainian scale (ticket to VIP bus of Autolux cost more, than bed in 4-berth compartment of sleeping car of 2nd class(Kupe) to the most expensive among overnight train), VIP departures of Autolux are normally completely sold-out, so buying ticket before departure is almost never possible.

But again, all this good only in Spring, Summer and Autumn. In Winter - if you trap to snowy weather or sleeper road - travel by bus can become very time consuming and dangerous, in winter - always choose the train.

Do they have night trains from Odessa to Kyiv

yes, all trains except the fasterst daytime IC+-one - contains only of cars, intended for sleeping or laying. At present there is no seating cars in overnight trains connecting Kyiv and Odessa at all.
If you are taking overnight train - no sence to exit in Vinnytisa, anyway you have too few time for sleeping, no sence to decrease it.

The idea of taking IC+ to Vinnytsia and then after exploring Vinnytsia continue by other train to Kyiv is doubtfull. Vinnytsia definitely don't belong to top 10 most worth to be seen cities of Ukraine.It's not bad, but better spend this time wherever else.

Uman arboretrum "Sofiyivka" is defitinely worth to be seen in May. But it's horribly crowded in this period, especially on non-working day, when half of Ukraine comes here. Regadring "Sofiyivka" in other time of year I'm really unsure if it worth. In Winter - definiely no. Anyway you don't need whole day in Uman, for exploring arboretrum you need may-be 4 hours, plus whatever you need to eat and rest.

I know there are buses from Chișinău via Palanca or Tudora to Odessa (http://terra.md/ro/timetable/gara_nord/default.aspx), but wasn't sure about the reverse route from Odessa to Chișinău via Palanca or Tudora.

There are plenty of buses from Odesa to Chisinau via Palanca (I think nowadays most of Odesa-Chisinau buses go via Palanca, thus avoiding Transnistria. You can check some schedules here - http://www.odessabus.com/en (it's half English/half Russian), but don't buy any tickets in advance. It will be cheaper and more reliable to purchase tickets at the bus station. 

Main reason is I want to avoid the train since it goes through Transnistria and though I have heard it's now easier to go through (no longer needed to get off the train and go to the police station), I still feel that bribery or harassment still happens at the border when going through the zone.

Besides Transnistria factor direct train also runs only couple days per week

Also I'm only seeing buses leaving later in the day from Chișinău, is there any options of going to Odessa earlier?

Yes, sure. It's just better to check Moldova bus timetable here -  http://www.garanord.md/orarul_rutelor.cfm (it's in Romanian, but everything is pretty easy - just enter Odesa and you will see dozens of buses per day) or here - http://www.autogara.md/orar/ (other bus stations in Moldova), although take into consideration Maxy's post regarding the weather conditions.

Next Question is from Odessa to Kyiv.  Since it's a fairly long trip, I was thinking the train, though I believe it goes out of the way via Vinnytsia while the bus goes via Uman'.  Do they have night trains from Odessa to Kyiv with sleeper cars at all or would it make sense to just take a train to Vinnytsia, stay a night or two and then go to Kyiv?  Or would the bus be better taking an early morning bus to Uman' staying the night or two and then on?

Well, Maxy partly answered your questions, I'll just remind than Ukrainian Railways now have decent website in English for the ticket sale - http://booking.uz.gov.ua/en/ (with most of the regular trains you can print your ticket at home). Among the overnighters most fancy one is the 106 branded train (22:25-7:10)

I'm trying to go from Chișinău - Odessa -Kyiv, but may end up doing it in the reverse order depending on flights so this is why I was asking about the reverse route from Odessa to Chișinău.

Yep, I guess flying to Kyiv might be a cheaper option. Anyhow, with those three cities in mind it doesn't really matter where you start. You can even go Kyiv-Chisinau-Odesa if you want

So I was thinking of going from Chișinău to Odessa to Kyiv for my 2 week trip.

Imho, two weeks might be a bit too much for those three cities, in Kyiv & Odesa you definitely can find something to do for 3-4 days, but Chisinau... well I would say 1 day maximum, it's better just to spend extra time elsewhere in Moldova or Ukraine.

Great thanks for both of you for the advice.

  And yes I would be going in May so not in the winter time.  How many days in advance would you need to book the Autolux from Odessa/Kyiv or visa versa?  Do you need to book in advance for the overnight train as well?  Usually I always just take day trains/buses and have always followed TuT's suggestion about getting tickets at the station the day of or the day before as I've often seen trains or buses that haven't been listed showing up with better times to my destinations in the past.

  There's also the option of just flying too from Odessa to Kyiv as it seems very cheap, if there's not a lot to do in Uman' or Vinnytsia?  But yes if I get the overnight train, I can just sleep the entire way and not worry about it.  Though I've never done an over night train before so would have to figure out the best way with the least amount of people in the berth.

  With my plans for 2 weeks then and not a lot to do in Chișinău (though I was thinking of taking a day trip to Transnistria from there), and Odessa and Kyiv, what other places then might be worth spending a night or two along the way instead of just those 3 cities then that's along the way?

  Thanks again and watch my trip end up being cheaper to go to Serbia this year, but I'll ask that if it changes in another post if I get a cheaper flight.  Haven't booked it yet, but really have my mind set on this one if I can do it...

How many days in advance would you need to book the Autolux from Odessa/Kyiv or visa versa?

May is not the beach season yet, so demand is not so high like in Summer.
The time when you are can be confident you'll got the place depends on weekday and the departure. The worst cases (the 18:35 departure from Odessa to Kyiv on Sundays and the 18:00 departure from Kyiv to Odessa on Fridays - it's better to buy in 3-4 weeks in advance. Other departutes usually are available if you buy in few days.

Do you need to book in advance for the overnight train as well?

of course. 4-berth compartment in overnight train if it's domestic travel - is cheaper than bus, thus trains are completely sold-out in kupe (4-berth compartment).
The more pricey 2-bed compartments remain available longer, but also will sold-out in May.

Usually I always just take day trains/buses and have always followed TuT's suggestion about getting tickets at the station the day of or the day before

In Ukraine it's usually not possible on most directions. Railway tariff is ridiculously low, but quantity of trains and quantity of places in them is definitely not enough.

There's also the option of just flying too from Odessa to Kyiv as it seems very cheap

please note, really low fares (499 UAH in case of early booking) is available only to one flight (opreated by BravoAirways), while for other flights of other arlines minimal possible price in case of even earliest booking is significantly higher (about ~1000 UAH).

Also important point is which airport of Kyiv depart/arrive the flight. Boryspil (KBP) airport is quite remote (almost 40 km from city center), thus travel time to this airport from Kyiv city center consumes quite much time (almost 1 hour), making total travel time from city center of Kyiv to city center of Odessa in total, including time reserve before check-in in total insignificantly smaller than going by fastest among buses, difference in travel time will be less than 1 hour. In case if you have flight to/from small Kyiv-Zhuliany (IEV) airport, which is located within city, in only 7 km from city center - flight save you more time, in such case taking flight save you ~1,5 hours comparing to going by fastest among buses. But  too few flighs are available to/from IEV, most flights are from KBP.
What is fancy - the flight of BravoAirways with cheapest minimal price - is the flight from IEV, while more expensive flights are usually from KBP.

But yes if I get the overnight train, I can just sleep the entire way and not worry about it.  Though I've never done an over night train before

oh.
You have interesting dilemma.

If you are curious to try travel by overnight train - Ukraine is good place for first experience, becase Ukrainian overnight trains provide very good quality/price ratio.

On other hand - there is one sad thing regarding overnight train - the abiity to sleep in overnight train is kinda skill.
If you are non-experienced - there is significant chance you'll be not able to full asleep all night and will be broken all next day. Those, who travel by overnight trains regularly - have kinda skill and become able to sleep, but you are not trained. But no way to check unless you try.
So you must decide by yourself.

so would have to figure out the best way with the least amount of people in the berth.

well, berth in 4-berth compartment is already quite good.
If the price difference with 2-berth compartment is not important for you - choose it.

what other places then might be worth spending a night or two along the way instead of just those 3 cities then that's along the way?

well, in the area around the places very worth a visit are Lviv, Kamyanets-Podilsky and Chernivtsi (each of them is more insteresting than  Chișinău for example), but they are little bit outside the way you've planned. You can replan your itineary to cover them. It's hard to give exact proposal unless you don't tell from where you arrive and where you continue. For example I know few foreigners, who wanted to visit Kyiv, few other cities of Ukraine and Chisinau and figured out it makes sence to do by circle with including the nearby part in Romania, something like Kyiv - Odessa - Chisinau - Iasi - Suceava - painted Bucovina Monasteries - Chernivtsi - side trip to Kamyanets-Podilsky - Chernivtsi - Lviv - Kyiv.
Depending on from where you come and where you continue later - you can try to find the flight with open jaw arrival/departure from different places on this circle, allowing you to avoid one of "longer" sections in this circle.

Thanks Maxy

  Yes I was noticing the 2 airports in Kyiv and am not sure which one yet I'll be arriving at (or leaving from) when I book my trip.  If it's KBP, then I just hope there's easy access by bus or train to/from the airport and the city center.

  With the over night train, I forgot that I have been on one once decades ago in Egypt.  I forgot about that, but don't remember too much about it.  I'm an on and off sleeper so having my sleep disrupted all through the night won't be an issue with me and I'll be fine the next day (one of the reasons I never suffer from jet lag in my life) so doing that wouldn't be an issue.  I guess though I would have to try and book the train then online then as you mentioned they will probably sell out.  Though I guess worst case I could just take a bus and play it by ear like that.

  If I can get my tickets for this trip decent enough, then I can try and plot a route to maybe include some of the areas you talked about.  And yes I was looking at maybe the bus into Romania and then up to Odessa (I've been to Romania before).  So that might even be an option as Chișinău seems by you and TuT that it might not be somewhere I want to spend a great deal of time in, so I could cut that down a bit and go elsewhere like you mentioned.

  I'll get more info if I can get a good flight deal then and then figure things out from there, but this gives me a good idea what I'll be looking at...

Do you need to book in advance for the overnight train as well?  Usually I always just take day trains/buses and have always followed TuT's suggestion about getting tickets at the station the day of or the day before as I've often seen trains or buses that haven't been listed showing up with better times to my destinations in the past.

Well, there is no unifying law here. Everything really depends on each particular country/connection. As far as I know, even in Ukraine alone for some domestic connections you would easily be able to buy good berth on the day of the journey, while on the other you won't be able to do it even a week in advance. Also a big factor is the potential presence of discounted tickets - UZ in this case isn't very progressive, so buying in advance is not essential in terms of money matters.

There's also the option of just flying too from Odessa to Kyiv as it seems very cheap, if there's not a lot to do in Uman' or Vinnytsia?

Uman' & Vinnytsia can be seen as stopover for couple hours-half a day, imho. I don't think it makes sense to stop there for longer time.

With my plans for 2 weeks then and not a lot to do in Chișinău (though I was thinking of taking a day trip to Transnistria from there), and Odessa and Kyiv, what other places then might be worth spending a night or two along the way instead of just those 3 cities then that's along the way?

Btw, besides excellent suggestions to visit Lviv, Kamyanets-Podilsky and Chernivtsi, you can always make a day trips from Kyiv or Odesa. E.g. with Kyiv it can be Chernobyl (if you up for this kind of things) or more usual places like Poltava or Chernihiv. From Odesa you can visit Bilhorod-Dnistrovskyi (and places around) and so on.

So that might even be an option as Chișinău seems by you and TuT that it might not be somewhere I want to spend a great deal of time in, so I could cut that down a bit and go elsewhere like you mentioned.

As was mentioned earlier, Chisinau might be good option for a day or max two, but it doesn't mean you can't spend more time in Moldova Since besides the Transnistria there are also other places to visit (e.g. related to wine industry)

I'll get more info if I can get a good flight deal then

That's a smart way, because local journeys in Ukraine/Moldova are rather cheap, so you should first of all think about flight to/from cheapest airport. While then it won't be very difficult to built logistics from there

On other hand - there is one sad thing regarding overnight train - the abiity to sleep in overnight train is kinda skill.

I think that if you had a full & busy day before the journey, then 90% of all people won't have trouble sleeping on the train

Ok sounds good and yes Chernobyl is definitely on my list if I can find a good decent tour to get there as I think that's the only way I would be able to do so.  That was one of the day trips I was going to take from Kyiv.  Ok will not bother with stopping over between Kyiv and Odessa then if I can help it, unless I can't get a over night train (depending on times and such or which direction I'll be coming from), but I could manage sleeping on the bus too if it came to that as well.  I've managed 14 hour flights before to India and 6 hour bus rides through Bulgaria so I should be able to handle the bus if I had to and just sleep on that if the train wasn't an option.

  I'll also look into a few of the other suggested day trips then from both Odessa and Kyiv depending on my time scheduled.  I'll get my flights (if possible) and then I'll have a better idea how to plan the trip then.

Thanks again...

Ok was able to get a ticket and be far enough removed from the Eurovision masses in Kyiv and I can watch it at a pub in Odessa.  So thinking now that I have my actual flights I can plan this easier using the two of your suggestions and some of my own.

  Flying into Chișinău at night on a Sunday and leaving on a Wed morning.  I figure since Chișinău didn't have that much to really do or see as you mentioned, I could take 2 day trips each day.  One going to Tiraspol on the mini buses they have (sine I guess you no longer need to report to the police station or show documentation of where you're staying if you are only staying under 10 hours in Transnistria.  The other day I was thinking if it was possible being that it's only 2 hours away going to Iaşi for the day.  Though I do remember last time I was in Romania, Moldova was still using the old Soviet train rails and taking a train between the two was long due to switching the trains, so not sure that is an issue anymore, or if a bus is more viable.  If not I could always just go see some of the underground wineries outside Chișinău  (or if there are any other day trips worth doing).

  Then taking the bus to Odessa and doing the beach (I know it won't be quite beach season, but I've been to Estonian, Croatia and Bulgarian beaches in May so I should be able to at least walk around the beach and enjoy that.  Plus it will allow me to do that day trip mentioned to Bilhorod-Dnistrovs'kyi.

  Then off to Kyiv.  Thanks for the inputs, so I've narrowed it down to either the bus or flying (if I can get a good flight to IEV), though the Skybus should be able to take me into town from KPB easy enough if I don't book in advance I hope.  Checked the train option but seems daytime trains are around 8-10 hours and the over night train would mean me having to wait around until 11pm or so without a hotel room to go back to etc.  Figure I can take the bus early Sat and be there in the early afternoon on a Sat and then check in and enjoy pub hopping Sat night in Kyiv.  Now I looked at autolux.ua, but since I can only read limited Russian/Ukrainian, I was able to see there is a bus leaving at 6am and getting me there around 12:30pm in April (since they don't have May time tables up).  I would think these would be the same times for May.  Now with that, I probably wouldn't need to buy my tickets in advance correct?  I'm just having an issue trying to locate the bus station (Hear it's at Kolontayevskoi 58), but can't find it on a map.

  That then leaves the rest of the trip in Kyiv where I'm thinking of doing the 2 night Chernobyl trip or something and then other random stuff before using the Skybus to KBP later on that week.

  This way I get ample late night pubs nights in all 3 cities and still get to stuff without having too many hotel bookings and staying a few nights in the same hotel before moving on.

  Thanks for the help you too, and every trip I always seem to have many questions...

The other day I was thinking if it was possible being that it's only 2 hours away going to Iaşi for the day.  Though I do remember last time I was in Romania, Moldova was still using the old Soviet train rails and taking a train between the two was long due to switching the trains, so not sure that is an issue anymore, or if a bus is more viable.

Well, change occurs only for the overnight Chisinau-Bucharest train, while daytime trains (i.e. Moldavian Chisinau-Iasi Socola 6:43-11:00 (runs only on Fridays and weekend) and Romanian Ungheni-Iasi (7:55-9:33 & 17:00-18:33) run without change. However most of the locals when traveling Chis.-Iasi would go for a (mini)bus option, there is even special day tours (morning from Chisinau to Iasi and afternoon/evening back to Moldova capital) or direct buses.

If not I could always just go see some of the underground wineries outside Chișinău

Definitely can be an option, good and cheap wine... why not

... I've narrowed it down to either the bus or flying (if I can get a good flight to IEV)

I think the company which offered cheapest flights here canceled the Odesa-Kyiv line, at least for low-season time, but, imho, bus option here is almost as fast (taking into consideration that you need to get to/from airports in both cities, security, check-in, etc.) and definitely cheaper

...and the over night train would mean me having to wait around until 11pm or so without a hotel room to go back to etc.

Odesa railway station has luggage storage rooms, so in case you change your mind, you can always drop your suitcase and spend those couple evening hours in a bar, theater, walking around, etc.

Now I looked at autolux.ua, but since I can only read limited Russian/Ukrainian, I was able to see there is a bus leaving at 6am and getting me there around 12:30pm in April (since they don't have May time tables up).  I would think these would be the same times for May.

True, even if there will be any minor change the early morning departure (and arrival around noon) would be there anyways. 

Now with that, I probably wouldn't need to buy my tickets in advance correct?

Yep, doubt that there will high demand for Sat. morning dep. 

I'm just having an issue trying to locate the bus station (Hear it's at Kolontayevskoi 58), but can't find it on a map.

Hmm... it seems like in Odesa autolux buses depart from a stop next to the main railway station. Kolontaevska 58 is where Odesa central bus station is located, but autolux neither in Odesa, nor in Kyiv uses the central bus stations

Ok that will work out then.  I can do the mini bus to Iaşi for the day then (I assume it would be at the same location as the mini bus to Tiraspol and Odessa?).

Then will do the bus then I guess from Odessa to Kyiv which seams the easiest.  I tried looking for Kolontaevska 58 before, but Google wasn't able to locate it for me, so your Google link helped me and I can check up on the time tables and such when I get there for the Autolux buses then since I'll have a few days to orient myself.  Also will need to find the bus to get to  Bilhorod-Dnistrovs'kyi and back as well, but I assume those would be at the main bus station if I can find it...

I can do the mini bus to Iaşi for the day then (I assume it would be at the same location as the mini bus to Tiraspol and Odessa?).

The official buses appear to be departing from southern bus station (so-called Gara de Sud), however un/semi official ones might be departing from other places (e.g. in front of the railway station or central bus station next to the main market or even pick you up from your location in Chisinau)

I tried looking for Kolontaevska 58 before, but Google wasn't able to locate it for me, so your Google link helped me and I can check up on the time tables and such when I get there for the Autolux buses then since I'll have a few days to orient myself.

Well, perhaps there was some issue with RUS/UA transliteration and google maps when you've searched for Kolontaevska. Central bus station in Odesa located here - https://goo.gl/maps/JBqHLWpv1gv (it's not very far from the center, however a bit further west than the main railway station)

Also will need to find the bus to get to  Bilhorod-Dnistrovs'kyi and back as well, but I assume those would be at the main bus station if I can find it...

It seems that at least some minibuses to Bilhorod-Dnistrovs'kyi depart from the main railway station (bus number 560), but since it's rather popular destination from Odesa, I won't be surprised if there is other minibuses to B.-H. departing from elsewhere in Odesa as well. From the main Odesa bus station on Kolontaivs'ka (see above for the google maps link) you can probably catch only some transit buses, but not direct Odesa-B.-H.

Thanks for posting those links.

As for Iași, I was reading that the one way trip could be 3-4 hours depending on the border.  That might be a little much to go for just a few hours of wandering around.  Might try and find something more local in Moldova that's an easy bus trip (plus being in Romania in the past, I probably should see all I can in my time frame of Moldova)...

Found the buses from Chișinău to Odesa (http://www.garanord.md/orarul_rutelor.cfm?S_ORAS=Odesa&ID=20910&CODU=208937&Grid1Page=1), though why do only the later buses in the day state Palanca?  Does that just means there's an official stop there while the early buses in the day just drive through Palanca and not stop?

  I know you stated most buses will avoid Transnistria (though I will have already visited there on the trip), just wasn't sure if these buses go through there or not?  Doesn't really say anything on the website.

  As for Odesa-Kyiv, found I can book the train 2 weeks in advance and that the first class will get me to Kyiv at a decent time in the day and only seems to be 1/2 shorter than the bus (unless like mentioned the buses drive faster in the day than the time stated).  Might be more comfortable on the train as first class opposed to the bus...

Found the buses from Chișinău to Odesa (http://www.garanord.md/orarul_rutelor.cfm?S_ORAS=Odesa&ID=20910&CODU=208937&Grid1Page=1), though why do only the later buses in the day state Palanca?

in fact palanca mentioned after dash in destination point (for example ODESA/PALANCA(GA)) - is optional.
If destination point don't contain this /PALANCA it doesn't mean bus doesn't go via Palanca.
Simply one bus carrier insisted their departure should be listed with explicit mentioning of going via Palance, other bus carrier didn't this and bus station simply list Odessa.

I know you stated most buses will avoid Transnistria (though I will have already visited there on the trip), just wasn't sure if these buses go through there or not?  Doesn't really say anything on the website.

it's wrong impression. Most of buses go via Palanca. Most of those, which are listed as simply to odessa and those where explicitly written via Palanca or via Tudora (it's the same way).
With present stupid design of Garanord.md website you can ensure the bus you like really go via Palanca only by making separate seach to Palanca http://www.garanord.md/orarul_rutelor.cfm?S_ORAS=palanca&ID=20822#ruta1
and findining in results all buses which you've seen in search result to Odessa. As you can see - almost all buses are here - morning, daytime and evening.

Does that just means there's an official stop there while the early buses in the day just drive through Palanca and not stop?

It means only garanord.md website could be better. It so stupid that their database "knows" intermediate stops, but don't allow to see them by clicking the departure.
but yes, the problem that intermediate point Vama Palanca is listed in one bus departure and missed in other, despite both go via Palanca - is possible too.
you can also try MAIACHI AS, STEFAN-VODA, STAROCAZ+, CAUSENI. If at last one of those intermediate point is present in bus route and then bus reaches Odessa - bus definitely bypasses Transnistria.

  As for Odesa-Kyiv, found I can book the train 2 weeks in advance

well, 1st class is not a big problem, Ukrainians almost don't buy it while seat of 2nd class are available, because find it too pricey. Only when 2nd class is gone - seats in 1st class start to sold-out quickly.

and that the first class will get me to Kyiv at a decent time in the day and only seems to be 1/2 shorter than the bus (unless like mentioned the buses drive faster in the day than the time stated).

Let me explain once more, may be it's will be more clear this way.

Daytime train takes 7 hours.

Convenient buses (the most of buses, I don't reccomend to use them) - have official travel time varying from 7:00 (and can be up to 8 hours), de-facto travel takes usually ~6:45. Comfort level - definitely worse than 2nd class in train. Try to avoid them if there is better option.

But there are few the fastest and more comfortable buses (not all Autolux and Gunsel ones, but only very few particular ones - the 6:00, 16:00 and 18:35 Autolux and 5:45 and 17:15 Gunsel) - have listed travel time 6:30, de-facto travel time will be ~5-5,5 hours. The bus which used for this departures provide higher level of comfort than normal bus, for example here is one type of coaches which used on such departures of Autolux
http://www.unvertur.com/images/safir_vip.jpg
there is only 28 seats (instead of standar 45) in 12-meter bus, seats stand 2+1 instead of 2+2 and more space between rows. Comfort level definitely better than 2nd class of train.
Those few particular bus departures (5 per day in current timetable) - are the only buses I've proposed you to think about.

  Might be more comfortable on the train as first class opposed to the bus...

But of course, in case of comparsion with 1st class in train - bus is worse, even such better one. In train there is more space. Rolling stock used for daytime train Odessa - Kyiv have 3,5 meters wide carbodies and in 1st class there is 2+2 seats. Definitely 2+2 seats in 3,5 meter wide car-body provide more space than 2+1 seat in 2,5 meter-wide bus.