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
I'm seriously considering importing a GU/Y61 Nissan Patrol but the configuration I want doesn't seem to exist in LHD so I may fall back to one of the above (LX470 or Xterra likely) out of convenience for a turn-key truck. If only they were solid front axle rigs. I don't want to go down the conversion road yet again.
I love my XJ - it's the right size for wheeling and dealing with my family of four. The drivetrain is great, especially after the modifications I've made to the axles but the "Chryslerness" of the interior constantly pisses me off and I'm going to have to do some work to bring it up to my expectations going forward (sound deadening, address fit/shim, even more unibody stiffening).
The WJ is a bit better - at least the unibody is stiff enough out of the box (thanks Porsche!) but it still has a craptastic Chrysler interior. I almost bought one last fall for a winter vehicle but ended up with another XJ just out of a sense of... well... contempt/familiarity/value I guess.
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.
After those two things the less electronics the vehicle has then the better (later Land Rovers can be a PITA because of that).
Some of the vehicles above don't match these criteria.
Also, keep in mind that old vehicles are just that: old.
2¢