Martinjmpr
Wiffleball Batter
Sounds like a 3rd gen would be a good choice. FWIW I sold my 3rd gen in June for $5k. This was a 99 "tall coil" SR5, 3.4, auto with the rear E-locker and 150k on the clock. Had a lot of lookers but only one serious offer and I was in a but of a hurry (I had a trip coming up and needed my new vehicle to pull our trailer.)
One of the nice things about a later (99+) SR5 is that they have a lot of little "perks" that are not really neccessary, but nice to have. Things like 3 power outlets in the dashboard and one in the rear, better cup holders, auto up/down on both front windows, nice alloy wheels, a separate heater for the back seat (with the fan under the front passenger seat), an automatic headlight shutoff that keeps you from accidentally killing your battery, and probably a few other things I've forgotten. Of course, they almost always have the power antenna, too, which is almost always broken (mine sure was - I just pulled the wire to the motor and left it up all the time.)
Couple of things to note, however: Noise-wise, I don't know what your Cherokee is like but I found the 1st gen Taco/3rd gen 4runner (same basic platform) to be rather noisy at highway speeds. It's probably a relative thing, though. Given both the boxy, wind-assaulting shape of the Cherokee I'll bet the 3rd gen is quieter but maybe not by much. My 4th gen 4runner is noticeably quieter than the 3rd gen, which is nice.
Another thing (and I harp on this a lot because it was a big deal to me) the gas tank is a tad small IMO. 18.5 gallons which at normal MPG of 16-18 will give you, at best, 300 miles of range before you need to fill up (and that's being optimistic - around town expect your low fuel light to come on between 215 - 240 miles.) The fuel gauge is also notoriously inaccurate, so you'll want to run a few tanks to make sure you know what your range is (we actually ran out of gas in my 3rd gen in Oregon back in June, but that was due to a combination of pulling a heavy trailer through the mountains and not filling up when I should have, so I can't blame the truck for that one.)
Off road you will find the 99+ 3rd gen superb, even with the factory suspension. The J-shift T-case is pretty much bulletproof and the 4runner can probably handle just about any trail you're brave enough to point it down.
One of the nice things about a later (99+) SR5 is that they have a lot of little "perks" that are not really neccessary, but nice to have. Things like 3 power outlets in the dashboard and one in the rear, better cup holders, auto up/down on both front windows, nice alloy wheels, a separate heater for the back seat (with the fan under the front passenger seat), an automatic headlight shutoff that keeps you from accidentally killing your battery, and probably a few other things I've forgotten. Of course, they almost always have the power antenna, too, which is almost always broken (mine sure was - I just pulled the wire to the motor and left it up all the time.)
Couple of things to note, however: Noise-wise, I don't know what your Cherokee is like but I found the 1st gen Taco/3rd gen 4runner (same basic platform) to be rather noisy at highway speeds. It's probably a relative thing, though. Given both the boxy, wind-assaulting shape of the Cherokee I'll bet the 3rd gen is quieter but maybe not by much. My 4th gen 4runner is noticeably quieter than the 3rd gen, which is nice.
Another thing (and I harp on this a lot because it was a big deal to me) the gas tank is a tad small IMO. 18.5 gallons which at normal MPG of 16-18 will give you, at best, 300 miles of range before you need to fill up (and that's being optimistic - around town expect your low fuel light to come on between 215 - 240 miles.) The fuel gauge is also notoriously inaccurate, so you'll want to run a few tanks to make sure you know what your range is (we actually ran out of gas in my 3rd gen in Oregon back in June, but that was due to a combination of pulling a heavy trailer through the mountains and not filling up when I should have, so I can't blame the truck for that one.)
Off road you will find the 99+ 3rd gen superb, even with the factory suspension. The J-shift T-case is pretty much bulletproof and the 4runner can probably handle just about any trail you're brave enough to point it down.