That is a decent price for a '99 XJ, providing the drivetrain and general condition of the vehicle is acceptable. A 2-door with manual transmission is rare and fairly sought after, and a '99 is considered the best "stock" year of the XJ breed. This likely means you have a high pinion front Dana 30 axle and a 29-spline Chrysler 8.25 rear axle. If that is the case, 33" tires are plenty strong for that configuration, and some will argue they are suitable for 35" tires. If your rear differential has a flat bottom, it is the preferred Chrysler 8.25, which is as strong as a Dana 44. If it is round, you have the less strong Dana 35, which you don't want.
Speaking of differentials, see if the PO installed gears and/or lockers. Both will dramatically increase the value of this Cherokee. With 33" tires, you'll want 4.56 gears to make it drive like stock, and 4.11 gears as a minimum. Stock gears were 3.55 for this year and not a good match for that tire size. Gearing is typically the largest expense you will encounter during your build-up, unless you have tools and made skills to do the job yourself.
I suggest inspecting the engine compression and after market suspension. At 144k miles, this XJ is only middle aged and you should exceed 300k miles with routine maintenance. The I6 is a very good motor and a little care will take you a long way. My current Cherokee is just under 150k and it drives like a dream. Common problems for this year XJ include failed engine mounts and cracked exhaust manifold. Both are very easy to repair and upgrades are common with moderate expense. Again, check those for condition and use for a bargaining tool if cracked or failed. Plan on buying Brown Dog motor mounts (search) and an aftermarket manifold. Both will only set you back 500 bucks and you can do the job yourself with minimal time and trouble.
There are many lift kits available for the XJ, but you need to watch out for improperly built and installed kits. Lift blocks should NEVER be used on an XJ and scrounged parts usually spells trouble. Make sure your control arms appear solid and properly attached, track bar is of proper length to center the front axle, brake lines are of adequate length for suspension flex, and all connection points and ball joints are secure and in good order. A good option for a 4"+ lift are full replaced leaf springs and longer front coils. Pucks on top of coil springs and blocks on top of leaf springs spells ass-hattery and should be avoided. This may sound dumb, but if all suspension parts match in color (gray, red, etc), the lift probably came as a kit, which is a good thing (but not necessarily bad).
Since the PO took the time to install a winch and aftermarket bumper, my guess is he knows a thing about the XJ and wheeling. Look for damaged rims, scuffed suspension parts, custom pinstriping, and the presence of skids, tow points, and rock rails to detemine build integrity and overall knowledge of the vehicle. Trail damage is normal but it may speak volumes for the overall condition of the vehicle.
You will also find a passenger window inoperative, intermittent driver's speaker, broken center console latch, and engine ticking noise. All are common and easily repaired. Make sure the Jeep has a slip yoke eliminated (SYE) as part of the lift kit. With 33" tires, it has probably been lifted to 4" or more, making an SYE and CV style rear driveshaft necessary. Search if you don't know what this is or how it looks.
Older vehicles, especially lifted Cherokees, may suffer from death wobble. Drive this around at speed and hit some bumps. If the steering wobbles uncontrollably and you soil yourself, you have death wobble. Some repair to the steering and/or suspension components may be necessary. Search for death wobble if you need to. This has driven some to madness, while others have resolved their problems with simple fixes.
Why did I say the '99 XJ was considered the best year Cherokee? It came stock with the best flowing intake, HP Dana 30 front diff, strong Chy 8.25 rear axle, reliable NP231 transfer case, AW4 tranny (not yours), newer body style and interior, stronger head (2000+ was prone to cracking), and the last year of the distributor/plugs.
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