I've been an XJ owner for a long time. I started with a '94 about 15 years ago and currently have a '99. The '94 was modified but noting too crazy. A lot of upgraded parts but close in function to factory. The '94 is currently with another family member and may be toast. I picked up a '99 from a buddy about 10 yeas ago and it was my mom's daily driver (less than 10 miles per day). I paid $500 for it and the plan was to make it project that I could restore from soup to nuts. Thus far, I have not put much work into the '99 and it looks a little rough. Long story made extremely short, I never had a single electrical problem with my '94 beyond the usual cluster connector problem and the power locks/winnows were failing. However, the '99 has been a nightmare since I have been able to start working on it. I fix one short or electrical component just to find another problem. The ~$3,000 question is, knowing that I want to keep this thing forever, do I keep the '99 with OBDII and added creature comforts, or do I try to find a second gen with less headache. While I enjoy working on it and learning how to fix a vehicle's electrical system, I cannot help by envy the time I had with my '94. Am I wrong to assume the older model is easier to work on and maintain for the long run, or was I just lucky with my run on the '94? Is this '99 just a particular pain in the *** or is that every '97+ model?

For example, since I took my '99 back (6 months) I found a ton of damaged wires where the insulation burn/broke off that caused a lot of problems, a tps code caused by a bad clock spring, speaker/radio issues, noting on the cigar/defogger accessory strip works, doors/windows/side mirrors work intermittently or not at all, same cluster issue as my '94. I know everyone worships the '99 but I am looking at this from a long term maintenance perspective. Any comments would be appreciated.

 

Basically, all Chrysler manufactured Jeeps have similar problems. There is a little more room in the front wheel wells on the Jen2 - otherwise the 1997-2000 are your best bet

 

The fact that the later ones have OBDII and the associated easy to access diagnostics is a huge issue to me.

Edit... longer story
I had a 96 I bought new, manual transmission . Only real issues I had was rust(including 2gas tanks that rusted through from the outside). Mechanically and electrically it was trouble free for the 15 years I had it when it rusted out.

I now have a 2000 I bought 8 yrs ago with 150 k on it. Now has 200 k with oe uncracked head. only electrical replacement were coil rail and cam position sensor....and it has a rust proof plastic tank. I did have to replace the heater core.
I think the real difference between individual 25+ year old vehicles is what sort of maintenance and abuse they have suffered over the yrs.
If I had my choice I would get a 97-99.