These are questions which, admittedly, mostly pertain to Eastern US properties. Might apply elsewhere.
For properties with buildings:
-How close is the nearest fire department? Will they have access to a fire hydrant on your property (probably not)?
-How close is the nearest snow plow staging area to your access road?
-What does the wiring look like? Do you have a modernized electric panel? (knob-and-tube wiring is still a thing in some houses. Many homes have chimeric electrical set-ups.)
-What is your critter tolerance? (expect at least 1 palm-sized spider in your house each fall, snakes in the outbuildings etc.)
-(if you don't have county water) How is your septic handled? Per county ordinance, what changes to your house would force you to upgrade your septic? (adding another bathroom etc.)
-What is the quality of the well water? Is there coliform bacteria? How do you plan to mitigate contaminates like lead, silicon, or copper?
-How do you plan to deal with power outages (there will be outages)?
-What is your well depth? Can your pump be easily powered by a generator during outages?
-What does the structural integrity of your house look like? Are the beams in the crawlspace supported to modern standards? Is there termite damage?
-If you are planning to use wood burning stoves as a heat source, do you have easy access to hardwoods to burn indoors (do not burn pine 'n sheeeet in your woodstoves. Beware creosote.)
-Do hire a good home inspector that is familiar with the baseline of your area-they'll be able to walk you through all this and more.
If you want to add a livable structure to a property, I don't have much firsthand experience. I can tell you from secondhand experience that you'll want to spring for perc testing BEFORE purchasing a property, if you are planning on adding a house to a property without municipal water access.
Hope that helps!