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I had a 3" Rough Country on my '99 XJ and it was fine. No problems what so ever. Then later I added a budjet boost and shackels and it looked a lot better. It did need a track bar though but it got rid of it soon after. Now I hav a '98 5.9 and a '92 XJ again.
I have driven Jeeps with multiple different lifts. From the short stubby AAL to the long AAL to the long with an extended shackel. The ride is definitely firmer. Maybe harsh isn't the proper term to use but stock they are so soft an AAL with make it harsher IMO.
I am on Jeep number 5 now and...
The only thing I noticed on my '99 was a little over an extra mile per gallon. Which is nice considering it gets crappy mileage anyway. If I had to do it over, I would make my own for about 1/4 the price.
Sounds a little overboard for a total of 3" max lift maybe. An 1" from the upcountry + 1 3/4 for the coil spacer and a shackle in the rear will barely net 3" of lift. I wouldn't bother with a tranny drop kit to start. Maybe with 5" but not 3". Also, remember not to get a shock for a 3" lift...
Just run to Sears and pick up a pair of spring compressors for $25. The only thing you would need to unbolt is the swaybar and shocks. Then if you still need more room, use another floor jack and jack up the opposite end you are working on. Piece of cake!
Good luck.
Use alot of WD-40 on the nuts and bolts you need to remove. Soak for several days to ease the removal. Otherwise, it's a pretty easy job. If you got new shocks, good luck with the rear upper bolts. My '99 broke three on the removal. What a PITA.
I don't mind the Rough Country lift. I bought the 3" with the full length add a leafs out back. Definately stiffer than stock but the stock Cherokee rear is too soft anyway. I don't like the shocke that came with the kit though. You could buy the kit minus the shocks and then get some decent...
With only 24,000 miles on it, I'd say go for the lift. A 2" kit with 30 or 31" tires just makes the Cherokee feel that much more stable on the road. I have 4 3/4" lift on mine and no bad vibrations with BFG AT 31's.