Italy Rail Pass seems to pay?

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Two 4 day Italy Rail pass costs 290E.  We are planning 4 train journeys in April and I priced them out on Trenitalia: MXP-Rome(98E+), Rome-Sorrento(70E), Sorrento to Florence(100E+), and Florence to Milan-Bergamo (84E+).  I'm not sure if these prices - most of them are MINI include a reservation fee.  All are ES high speed trains which we prefer.  Will the extra reservation fees still make it cheaper to buy point to point?

Standard seat reservation fare for EuroStar trains is 10 EUR per seat, so you can yourself add it to the pass price. Unfortunately, but at the moment offer Mini is the best thing you can get while traveling on high-speed in Italy, but it really depends on day and train - earlier purchase->better fare. What we see for app. late March-April:
For MXP-Rome TrenItalia doesn't sell "Mini", but do for Milano-Rome (from 49 EUR + MXP-Milano from 7 to 11 EUR by train). Roma-Napoli "Mini" by EuroStar is from 19 EUR (+ 3.4 EUR for Circumvesuviana Napoli-Sorrento); Sorrento-Napoli same 3.4 EUR, Napoli-Florence by EuroStar from 50 EUR, for Florence-Bergamo leg better to use two separate ticket, since anyway you will need train change (Florence-Milan 'Mini' from 19 EUR, Milano-Bergamo from 4.05 EUR). All the ticket for EuroStar already include seat reservation.
As result, while adding all of the above we get around 160 EUR and maybe for most expensive legs like Milano-Roma and Napoli-Florence you can even get a bit cheaper rates, since we didn't check all the dates and trains.
Resume: depending on date and train purchasing point to point with "Mini" offer might get you a cheaper travel at the end, but you need to check all the preferred trains and purchase tickets in advance.

Thank-you for your help again tUt.  I suspected that the reservation fees would make the pass less advantageous.  That would make the pass cost 145 + 40 EUR.  I just couldn't read anywhere that the mini fare included the reservation fee.  Now I have to decide if the convenience of a pass is worth the extra 35 or so EUR.  I worry that we'll miss a train and then have to buy another ticket at full price.  Then there won't be any advantage at all of point to point.

Is it very much trouble to make a reservation? Can it be done just before we get on the train?  I don't think we'll have a computer and will have to do everything at a train station - in English.

Now I have to decide if the convenience of a pass is worth the extra 35 or so EUR.  I worry that we'll miss a train and then have to buy another ticket at full price.

As we already noted, since we counted that extra not tied to a specific trains (but chosen randomly), then the best thing for you will be just to recheck for your desired connection on your desired date. Than you will exactly now "the extra" and can make your mind.

Is it very much trouble to make a reservation? Can it be done just before we get on the train?

It is not very complicated thing, but you might encounter some queues and potentially even "fully booked" trains (really depends on time and date), especially since there is a limit for passholders.
TrenItalia website as well offers reservations for passholders online, when selecting a price of your journey, you need to click on "more fares" and chose "Global Pass". 

Thanks.  I didn't know about the global pass option.