Congratulations on your decision, Toyota brand cars are one of best decisions with the least amount of risk in general.
Now I would suggest at least trying to buy your new truck South and inland of Pennsylvania. I am originally from the Philadelphia area, and Pennsylvania loves their salt on winter roads. And New England is almost rated worst condition used cars every year. Also drivers are more trended to start and stop instead of highway mileage.
Just look if you can go to Maryland or inland Virginia, cause you will be much happier I think. I also lived in Boston for College, Vermont for prep school for 2 years, my sophomore high school year was in Portland, Maine, and my freshman year I lived near Watkins Glen
I was a semi-pro sponsored snowboarder back then and attended private schools who catered to snow sports athletes of that age,some trying to go to the olympics, professional, sponsored, high end competitions act...
One you pass the Mason Dixon line, those southern sentiments of prizing their cars and trucks really comes on strong and their seasons tend to be less harsh and use of salt is almost non-existent
If you want to do mods, I personally think the 2nd or 1st gen are a better choice for a weekend warrior/offroader.
For the most expensive price of a 3rd gen, you can get a great condition 1st gen with more reliable engine, and spend half of the money you saved into a new paint job and BOSS high end equipment.
The first gen has a removable roof, a quality I dream that Toyota would bring back, but for the ridiculously safety conscious population we live in I do not see that coming.
If you want a basic OEM 3rd gen 1996-2002 3rd gen 4runner you are going to spend around 8-10k, for a 2nd gen around 4-5k for an excellent condition low mileage beauty or about the same price or 5-6 for an excellent condition 1st gen. so that leaves you about 4000 for a lift, wheels and new tires, bumpers & winch, and sliders. All brand new, exactly what you want and know they were installed.
you would almost have some cash left over to change the oil, transmission fluid and filer, and flush the differentials and maybe do a valve timing or a timing belt.
Consider the many options, maybe you just want to buy something and start using it and not have much to do, but I always say if you are going to take your family, you would feel much better knowing you have a reliable & safe vehicle. If you have to learn along the way, even better, cause then you can learn about the truck and possibly how to fix something in the future.
Try Craigslist, cars.com, ebay, auto trader
good luck, hope to hear you make a purchase that makes you happy