1) It's a great space is inside boston city limit, with a heavy deer/animal population, every winter.
2) The trees are not planted in the fall where the root system has a chance to become established.
3) The trees are planted in late spring/summer and they aren't watered to get them thru the 1st year
4) Native like pawpaw survive but European imports like apple/pear/plum are very suspectible to pest and die quickly
Because of the unique space, I would recommend the following.
1) Setup a drip irrigation system
2) Setup a dutch clover lawn that is 6inch, for nitrogen and also so that the edible can be easily identified and taken care of by the groundskeeper
3) Plant more natives like: blueberry, raspberry/blackberry, persimons, pawpaw, elderberry, native grapes, maypop, native hazelnut, etc
4) Plant more exotics like: mulberry, figs, goumi, akebia vine, artic kiwi vine, honeyberry, yellowhorn nut
5) Avoid the European imports like apple, pear, cherry, plum, peach, if you must plant the native or Asian species like beach plum, sand cherry, asian pear, etc
6) Don't accept the donation of half-dead trees in June and plant them
7) Plant in the fall for a better root system and less watering, and less deer/animal damage
8) Plant bare root, so that the plants are planted properly.