Since I'm such a 5-speed nut, how likely is it to find a 2000ish Montero (non sport) or Trooper with a 5-speed? What are the lifespans of the automatic transmissions on these? I've personally had bad luck with auto vehicles, the few I've owned started slipping and leaking around 180k.
Also, my budget has increased to closer to $5000 for purchase, which opens things up quite a bit. I'd like to try to get a 2000ish+ vehicle for safety reasons and such (wife was complaining about hauling our future children in an older vehicle with lesser safety features). Can't find a 5-speed on any of the rigs I've been looking for (within a reasonable distance) so I'll probably be settling for an auto.
The Trooper is definitely a top notch rig. I saw that it and the Montero we very closely matched, but what got me on the Montero was the 9.5inch ring gear and 4.62 factory gear ratio. Plus they can be had with an air locker from the factory. I got the LS which didn't come with one stock, but I installed one out of an SR. Very easy and didn't cost squat. I wouldn't hesitate to get a well taken care of trooper though. Check out my build thread if you wanna know more.
Since your budget has gone up a little... if I was looking today my "complete" short list would include:
Xterra
FZJ80/LX450
UZJ100/LX470
Discovery II (I'm a masochist)
Range Rover Classic (solid trucks)
Fourrunner (2nd - 3rd gen - but I personally don't fit)
Montero
Trooper
LR3 (see Disco above)
full size Grand Wagoneer that's already been gone through "just because"
Various "baby" Jeeps
Ford Explorer
...
That being said, I like being able to stop at a local store for most parts and being able to get them off the shelf for not a lot of money. It's borderline ridiculous compared to some vehicles.
Consider the safety aspects. To me front air bags on both sides of the vehicle are mandatory.
Also, fuel injection is mandatory.
...
The Xterra my coworker is selling is pretty overpriced. It's an 03 supercharged 2wd, with flat bald tires, faded paint, headliner hanging down, absolutely trashed inside. He can't figure out why in over a month of having it for sale he hasn't had any interest.