We currently own an 05 Montero Limited and it is by far one of my favorite vehicles. Just for reference, I've owned a 66 FJ45 Land cruiser LWB pickup, 1975 FJ40 Land cruiser, 1989 Isuzu Trooper, 1989 Suzuki Samurai, 1992 Isuzu Trooper, 1998 Isuzu Trooper, 1991 Montero LS, 2008 Toyota FJ Cruiser, 1989 2 door Montero, 2008 Toyota Tundra, 2011 Subaru Impreza Outback et al.
I picked our Gen 3 up with 30K miles on it last year. At the time, I found another 06 with only 4,500 miles on it, the dude just bought it and left it at his vacation home but I lost it to a higher bidder and I had the out of state disadvantage. A few weeks after picking mine up, I saw another 06 on ebay with only 3 or 4K miles on it. It looked like it had just sat in the garage since the day it was purchased. Any low low mileage 2005-06 Gen 3 is still gonna cost close to 20K but in my opinion it is still a better buy than any new SUV on the market right now that is gonna cost double that (4-runner, explorer, tahoe, etc) You can easily find a nice 03, 04, 05 with 60-100k miles for like 8-12K though. It seems like there were more options and models from 200-2003 and then 03-06 they all came with the same standard and fully loaded features. The only options I am aware of are between 03-06 you could choose between big sunroof or ceiling mounted DVD player. I think 05-06 also had bigger 17" wheels. If you haven't noticed a theme yet, go for 03 up they are more modern with safety, better engine, etc.
How do you plan to use you're vehicle? If you are a hard core wheelin type, I like the 1st and 2nd gen types better. That is why I own one of each! More options with body lifts, mods and such. The 3rd Gen, especially 03+ is very smooth and feels much more high quality to me. I've noticed almost every used gen 2 the leather seats and interior look like crap, just cheap. (no offense Gen 2 guys, I'm sure there are some nice ones) The 3.8 motor in the 03 and up is actual "Mitsubishi" not Dodge like the former year models. That is a huge plus right there along with a great automatic transmission with manual shift option. The 03+ also has Vehicle Stability Control, Traction control which is amazing in mud, snow, etc., AWD vs 2WD or 4WD. I like being able to select between them all. 4 wheel disc brakes, and the unibody construction just handles better overall on the road. rear seat folds down into floor, rear A/C and Heat (literally a seperate AC unit in the rear so it works well)
I want soo bad to modify my 05 but it is currently the family wagon so I will probably just go with an ARB bumper for now and maybe lift/snorkel/winch later on when the wife gets a new ride. ARB has a decently priced lift, you can fit 33's, ARB winch bumper, snorkel, lockers are all available so it could still be a pretty sick truck for off road with a few grand in mods and a very refined truck for everything else. I love them, I've considered buying two! One thing to keep in mind, you do have to do a fairly pricey timing belt/service every 60K miles typically around $1500 I hear, so keep that in mind. If you maintain them though, they'll last you a long time just like the old ones. I say go for it.
www.cars.com is your friend, hold out for a good low mileage truck and keep it forever. Good luck
