Just my 2 cents but I think the deal with Jeeps, especially TJ/LJ's, is that there is almost always someone willing to pay that high price. I think the dealers know it and I think private sellers typically know it too. I think there are also some factors unique to TJ/LJ's specifically that skew pricing and muddy the waters a bit.
- Often a second vehicle, used for rec purposes only, not a DD. Seller might not necessarily be motivated to sell quickly
- Often modded out, beauty is in the eye of the beholder type -ish. For some people (me), I was looking for bone stock. I don't need/want your crappy DIY mods and I dont need/want rock crawler mods - I couldn't afford the worthwhile ones anyway even if I did want/need them! Stock can be harder to find though and scarcity means higher prices as we all know.
- Often an impulse buy; whether you're a young kid looking for a sweet first ride or approaching your mid-life crisis, Wranglers seem to fit the bill for a lot of impulse buys at any age. Again, as we all know, an impulse buy often does not require a lot of logic or dispassionate decision making. People will spend too much to get that ONE TJ/LJ they've been thinking about for X months/years.
I purchased my '04 Sport for (I think) about $11.5 - it's an automatic and it came with around 95.5k miles. It's got normal rust and also some I didn't know about when I bought it but really is in pretty great shape considering I live in the midwest and we definitely get ice/snow and we definitely salt. With responsible upkeep and due diligence, I have no doubt I can get many many more years out of it as a DD, hopefully keep forever if life is kind to me.
At various times, I have felt that I both underpaid and overpaid. I probably overpaid a little but I also saved a lot of time that would have been spent searching, driving to see one, being disappointed, driving home, repeat. All that to save maybe another $500? MAYBE $1000? Not sure it would have been worth it.
Knowing what I know now, yeah I'd do some stuff differently but I love my Jeep and I have a blast driving it even when it absolutely sucks to drive. And I know I would have spent roughly the same amount or a little more to get a perhaps newer/safer/more gas efficient car but I don't think it would have had nearly the same charm or fun appeal. Also, I think I can get a good resell price if it ever comes to it with the way I baby this thing.
Sorry for the essay!