I currently have a 362XP modded to a 72cc, a stock 365 and 2 262's as well as some 371/372's.
It all depends on what your preferences are, the 365 is upgradable to a 72cc saw by swapping out the piston and cylinder (assuming you have the walbro carb), but is a bit heavier and slightly less power in its current 65cc form, If something bad happens to it, no need to fret as parts are very easy to get for it and likely will be for some time. The 372 class of saws are very popular and common.
The 262xp is a classic, sought after saw and if kept in good shape should go up in value, It is both lighter and has more power than a 365 although you wont be able to increase its bore size by changing out the jug. Parts are becoming somewhat scarce, as I'm restoring 2 of them and its been tough finding decent parts. Personally I like the 262's more but I probably won't use them much.
So I suppose if you want a saw that is going to get well used and tossed around a lot I'd go with a 365, but if you do only limited cutting and like to keep your saws pristine, and want all out performance for its size, then go with a 262. Both are great saws, and you can't lose with either one.