Like I said previously - the early Chevrolet's like to rust - this has the original paint.
These are all cool rigs, but with so many GMT400 and GMT800 Tahoes and Yukons out there for even money and better features, reliability and repairability, its hard to make a case for a recreational vehicle being an older 2 door SUV. I had a Ramcharger. Lots of fun but a total heap.
I had an 81 K5 for 14 years. Was into 4X4's when I lived in Fairbanks, Alaska. Bought the truck there. Drove it coast to coast twice. Would still have it if someone didn't run a red light and T-boned it by the left front wheel. Mine had a 250ci I6, TH350 AT and 4WD, supposedly didn't make that combo but had the window sticker in the glove box. Terrible mpg, a small V8 would probably get better. The I6 was short a leaf in the springs so it sat a bit lower. Never lifted mine. Can go to 33" before a lift is needed. I ran 31" because of cost. Auto-locking hubs that you back up to unlock can be changed over to manual, recommend that. 77 had the full-time 4WD and can be converted to part time w/manual hubs and something in the transfer case, forget exactly what. Haven't messed with 4WD since my K5 went to the junkyard. Late 60's to 74 (I think) top came off completely. After that only came off behind the cab. Solid axle w/leaf springs front and rear.
Bronco's were twin-I-beam front suspension. Coil spring front. Better ride but harder to lift. Can get the 300ci I6 or couple size V8, 302 & 351. Think the top comes off behind the cab on those on the 70's ones. Doesn't come off on later ones.
Ram/Trailduster. 318 or 360 V8. Full top and back hatch lifts up like a hatchback in one piece. K5 & Bronco window retract into tailgate and tailgate lowers. Solid axles w/leaf springs front & rear. Came in full-time 4WD in some years and part time 4WD is the later years.
If your get a full time 4WD and convert it to part time, mpg will improve but there is another side benefit. Full time shift options are low-lowlock-neutral-high-highlock. When converted to part time 4WD it becomes low2WD-low4WD-neutral-high2WD-high4WD. So you gain the option of 2-wheel drive in low range. Standard part time has high2WD-high4WD-neutral-low4WD. No low2WD. Don't really need that option very much but have ran across a couple times when I wish I did have that option. Needed to pull a lot of weight a short distance on pavement. Had to move a stuck truck and 5th wheel camper once. Trailer was on pavement, truck was stuck just off pavement. Pulled both a few feet to get the truck onto pavement. Used low4 because that's what I had, wished I had low2WD option at that time.
Rust in the rockers, around wheel wells (especially rear) and around tail lights. At least on the K5. Typical Chevy truck rust from the era.
Being a car guy who grew up in the early '80s (not that I really grew up) I'm familiar with all three of those. They each have their weak points but none of them have chronic issues that would make me not want to buy one. They're also old and popular enough that there's a fix for every problem one might have. The challenge with a challenge budget, particularly in New England is going to be finding one that's not rusted all to heck. I'd avoid a diesel GM for sure, try and avoid one with a lift kit and buy the nicest, least rusty one of whatever brand I could find.
had a boss who had a bronco. I think he has the tailgate fixed twice due to rust
The ramcharger was available in 2wd with the slant six and overdrive 4-speed, which would be the mpg champ of the group. The 4wd Dodges prior to '83-ish would most likely be full time too, so look for the lockout front hubs if you want to get double digit mpg.
There was a Blazer option in the 88+ Chevy body style too, and while the ifs is thought of as less capable off road it's enough better on road to make it arguably the most comfortable option. You also get TBI and overdrive, so basically it's the most modern technology option all around.
Yeah, it's tough finding what I want in a "challenge" budget.
What I am finding in that price range are the full size GM SUV's of the 90's and early 2000's. I'm thinking about a 90's full size Blazer, Tahoe or Yukon as well, and maybe even a Suburban. They don't have that cool removable top, but they will almost surely have A/C. Those will also have reliable EFI and a SBC.
If I can find the Montero I want I will be selling my 04 Suburban. It's a 2wd, but that hasn't bothered me over the last 5+ years of ownership in the same area as you. It's an original TX truck so the rust is minimal compared to a full time New England car.
Yep- some of the early GMT400 trucks were available as a 2 door SUV. IIRC the original Tahoe was a 2-door. I'd go for one of those, personally. The A/C may not even suck.
Otherwise- Blazer/Bronco/Ramcharger, take your pick. In my book they're all about the same. I love the Ramcharger styling myself the best, but I doubt you could go too far wrong with any. Get a small V8, stick an aftermarket intake with a 650 Demon carb on it, dual exhausts, and a $1000 aftermarket A/C setup, and have fun.
Bobzilla wrote: K5's "full time 4wd" is easily changed to part time with a set of Warn hubs. That, with the 6.2L Diesel and 700R4 with 4.10 gears would run 80mph all day long and get 20mpg. I'd look for an 86-87 with a diesel.
Actually it's a lot more than that, if it has the NP203 case. I mean, I guess you could just put it in 4H-Lock and leave it there with some manual hubs, but then you're still spinning the front driveshaft and axle shafts. Not gaining much there.
To do it right you need to convert the transfer case differential into an output shaft. Don't waste your money on the cheap 'wedge' style kits, which just replace the spider gears with small wedge pieces. Very weak over time. Track down a full replacement shaft style kit for strength. Then you also need a set of manual hubs too.
Even harder to find is the Plymouth Trailduster. Friend of mine had a 77 with a 318, full time 4wd, and a removable hardtop. Back "in the day" (late 80's) he purchased a soft top from JC Whitney. It was a tank, but alot of fun.
The Blazers with 305's seem to be less expensive. I've noticed just the past couple of years, after Jeeps became popular - new Jeep prices drove used Jeep prices which drove up old Jeep prices and then next were Blazers.
You may want to watch the Craigslist in the south, and have those of us that live there keep our eyes out for you.
I like them all (Blazers, Broncos, Ramchargers, Traildusters) and also Scouts
I think I need to move down south. 
https://tampa.craigslist.org/pnl/cto/6153030066.html
TWO Ramchargers for $1500!!!
Friend had a 78 Plymouth Trailduster w/318, manual trans & full-time 4WD. Was a tank. We used to go off-roading together, him w/his Trailduster and me w/my K5.
Almost forgot about the Scout II's but they are kinda unicorn nowadays. Have a soft spot for Scout's and Scout II's. Might be difficult to get IH engine parts nowadays though. May not be impossible, just a bit difficult.
But another one from this era to add would be the Jeep Cherokee/Wagoneer. Cherokee is 2-door and Wagoneer is 4-door but essentially the same other than door count. AMC engines and Chrysler trans. Some came w/the venerable 258 I6, not really powerful but near bulletproof. Small V8's too, 304 or 360. Also more or less unicorns nowadays.
Scouts and Cherokees are a little smaller, but still fill the "2 door old BOF SUV requirement. There's usually at least one 2 door Cherokee on CL near me- and the 4 litre 6 is a decent engine, if slightly ancient.
Is the real question "what cool classic SUV should I buy"? Let's not pretend this is a matter of practicality. 
I recommend shopping the Southwest and finding rust free. I shipped a car from Sacramento to Miami for $1200. That $1200 pays for a lot of rust repair. Plus you get a rust free SUV that would be like gold in your area if you want to sell it.
Don't even have to go too far away. There's good, rust-free stuff as near as Virginia and the Carolinas and Georgia, where, unless you're in the mountains, it seldom snows.
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