I believe this project is within my wife's and my capabilities. Hopefully if I ask enough questions and listen to the answers I can avoid making a lot of dumb and costly mistakes. I'm going to have to pull the trigger on the road and the lot clearing by next week to stay on schedule. I don't think the Forest Service roads will work. There are three wooden bridges that need to be crossed I'm pretty certain they won't handle anything bigger than a one ton. My GMC 1500 makes them creak.
More Pictures as soon as the land dries out a bit.
Three bridges are probably a non-starter -- permits, engineered plans and construction costs would be killers.
No doubt, this is within you and your wife's capabilities but you will need to pace yourselves and work smart to avoid letting the project grind you down to the point where it's just no fun. I think that is the psychological danger, the new project adrenaline rush wears off after 2-3 years
If you get your road serviceable, clear enough space and totally prep it for your first building project, that would be a good accomplishment for one season in my mind. Drop any trees on the perimeter of that area that lean towards your building location and expect a few wind-throws anytime you clear a wooded area, you will be exposing trees to wind they are not used to.
You need some time to walk your land and really understand and get to know it anyways. The existing vegetation can tell you a lot about the soils and moisture levels, plus observing this through a year or two of seasons is invaluable. Some test pits to confirm what you think are also a good idea.
Having a 'master' plan that is well thought out beforehand is the best way to avoid costly mistakes and do-overs. That plan includes everything you want to do or are even thinking of doing; the pieces drop into place in a logical way. You just can't come up with that in a couple weeks or months in my opinion. Developing that plan is the most valuable thing you and your wife can do this summer.
As you talk about your challenges I think more and more a 4wd construction backhoe with an enclosed cab, hydraulic thumb on the digging bucket and
grapple attachment on the loader bucket would be a great choice. Put a set of good chains on it and it will clear a lot of snow. You might need to hire an excavator for a few things, but that backhoe would cover a lot of bases and can transport materials like stumps, rocks, gravel, dirt, brush piles, building supplies, grade/maintain your road, dig trenches, etc. A decent used one will be expensive, but when add up what it does over the years, it is a good investment.
All master plans start with a list

I will start one and others will add to it.
Where to put your water well, pressure tank and supply lines so it serves the house and animals and will not be contaminated by manure runoff and never freeze up.
What sort of septic system? Composting toilet or water based? Grey water system?
A summer kitchen and dedicated butchering area with hot water and heat?
A wood-fired boiler that can heat all the buildings you want heat in, provides domestic hot water and uses your own firewood for fuel?
A sugar bush and sap house? I had a chance to taste pure red maple syrup recently, it wasn't quite the same as sugar/rock maple, but still quite good.
Root cellar?
Storage for a winter's worth of feed hay?
Tractor assessable composting area?
Wood shed?
Any drainage needs, french drains, swales, etc?
Storms come from north and northwest?
Kitchen garden?
Hen house?
One note about tree stumps, check out stump fences. The old timers used everything
stump fences - Google Search
Dave.