First off, the premise of this thread is a 3 saw plan, but one really should never fuel or sharpen in the woods/landing, and cold weather hasn't been factored either. Therefore:
Ported 346XP for most use but a 550XPG for colder weather or backup for fuel/sharpening, (see above) Ported Jred 2159 and 562XPG, again cold weather contingency. 372 XPG for cold weather and Dolmar 7900 for bigger stuff.
288 XP Lite, for biggest stuff. (Still in shop awaiting porting) School me on this CAD thing again.
Ha, who would hand file when you can just grab another saw? Honestly come on! Also the weather here gets cold but i could only justify a heated handle saw for maybe 1 month to 2 months max of the year. Might have to look into that!