I'll put my 2ó in here (these all assume your looking at top-of-the-line models):
As you've obviously determined, '95 (SR, of course) is a great place to start consideration. In
this discussion we talked about the different features available starting in '95 as well as things to watch out for - a few things not mentioned were the little things like headlight washers, infinity sound systems, factory fog lights, etc. These were nice options or sometimes standard equipment that the Monty saw throughout the '90s.
In '96, the Montero got a split second row which still fits 3 car seats across (I have 4 kids... <img src="/forums/images/graemlins/shiner.gif" alt="" />) and also got a passenger side airbag. Rear lockers were standard for the SRs from '95 to '96 (possibly '97) so you can't go wrong there.
If you can afford the extra $$$ I would personally go for a '97 SR as it doesn't suffer from the 2 major afflictions associated with the previous model years - namely, the valve guide seals which go bad around 100k and the lower intake plenum butterfly valves whose bushings can deteriorate over time. 1997 was also the first year that Monteros saw heated seats <img src="/forums/images/graemlins/butwiggle.gif" alt="" />. The downside beginning with that year is that, IIRC, that 3.5L engine produces about 10-20 less horsepower than it's older siblings. Again IIRC, '95 & '96 are the highest HP years that the Montero ever saw (before or after) although torque ratings did increase in later models.
If you don't mind the body style change (I've personally gotten used to the look & would consider one), what we refer to as the Gen 2.5 was produced from '98 to '00. These were the last years of the body-on-frame design, but things like leather & a rear locker are hit or miss on those models (although I've seen a lot of them with lockers). I like the idea that by the time those trucks were be produced, MMC had worked out the few 'bugs' that the 3.5 had, they were using higher quality leather on the seats and the tow capacity went from 4000 to 5000 lbs.
Finally, just so they're not left out <img src="/forums/images/graemlins/wink.gif" alt="" />, there's the Gen III (2001 & up) which I don't know a lot about except that it's unibody design, a 3.8L engine, the locker option was dropped (in favor of an electronic LSD), and has a neat 'stow n go' 3rd row seat (although why they went from 2 smaller seats to one medium sized one I can only guess at...). Most here seem to poo-poo it's offroad worthiness but I think it's probably more capable than people give it credit for.
HTH!
Shawn
