I test drove several Gen 2 and 2.5's in hopes of buying one. While I like many things about them, especially the 'looks' and a few key features, my wife and I had a hard time talking ourselves into that they were superior enough to our land rover Discovery ... that we just "had" to buy a Monty. Even in the reliability department, just about all the Monteros we drove suffered from a number of issues, all of which were repairable. They have a lot of characteristics many Japanese vehicles of the era have: robust running gear, less than robust interior and creature comforts. The doors sound flimsy and tinny when you close them. On the topic of ride and handling, the ones I drove (and it was several) seemed rather wollowy, and more top heavy in the corners than I expected, the the 2.5's were noticably better in the handling dept ....the earlier ones were quite a bit noisier too inside than I expected. The leathers they used might have been 'passable' at the time, but it must have been a lower-grade stock than many contemporary vehicles because it gets hard, cracked and falls apart easier over time than many others. The stock sound system on 96 and earlier was definitely substandard to the competion of the age in my opinion ....(but that can be changed, of course). As far as off-road goes, each vehicle is going to handle differently. Since 99% of my driving is on the road, that's my main focus. The little off-road driving I did with the Monteros that I tested, showed they can handle it ...and that's about all I need. That's just being an objective observer ... having owned and driven many SUV's over the years. There's no 'perfect' vehicle and I think on balance the Monty's got a lot of great things right ...worth owning one. But I have to say, it really made me appreciate driving my Land Rover more (warts and all -- and there are several). I'm still looking for the 'right' Monty .....and can't wait to get one, hopefully towards Spring. Actually, I'm thinking of maybe getting an H3 instead...
I think from an overall comfort and off-road standpoint, a WJ series (99-04) Grand Cherokee Overland is a fantastic buy. You get the 4.7 SOHC which is a screamer, neck-snapping power and throttle response and can pass people like they're standing still, Good handling, All the options, Solid axles front/rear, Very comfortable to drive, Nice leathers, Kick-butt sound system, Parts and service availability in just about any town, An extra inch of clearance (Up-country suspension only) ...and best of all Gerotor Veri-locking diffs rear, center and FRONT! No other vehicle in this class has that! You can basically be locked up front to rear ...or partially depending on the situation ...then drive out to the road and unlock automatically. I was initially skeptical, but I've seen it work many times. I went over to check on something by a rural property we own the other day and I parked in a neighbors field driveway because there was too much snow piled up on the roadside. This was a pretty steep driveway and there was about 4" of wet snow on the ground, and it was a muddy field driveway because the ground isn't frozen and we've had about 2" of rain lately. There is NO WAY, no way, I could have made it out of there with any other SUV or 4x4 pickup we own, or have owned. But I knew it would be no problem for the Jeep Overland. When I went to leave, it literally backed me out of there and up the drive to the road w/o spinning a tire! It's a wonderful system. Check some of the Youtube videos. If you have one tire that has traction, it'll get you out ...and the system doesn't rely on torque robbing traction control tricks that pause and require a lot of wheel-spin to engage.
There's a SUV off-road test, some S. African guy has a bunch of youtube videos (you can google it), where they put a number of SUV's to test up this particularly steep and rocky path that vehicles have problems negotiatin. Land Rovers (new and old), Toyotas ...don't remember the others they tested, maybe a G Wagon?. The Grand Cherokee, which costs a lot less ... with Gerotor diffs was the only one to literally walk right up it. I don't know that I would buy the plain-jane straight 6 WJ. The ZJ's were fine, but the WJ 6's that I drove weren't the same.
Anyway, there are a lot of good SUV's out there. The Montero is one of them. It isn't perfect but it is a heck of a buy for what you get and worth being a strong fan of them! I wish there was a greater parts support environment for these wonderful SUVs.