Considering an XJ or maybe a WK for for my kid

They are, but even when you do it seems like the XJ market is much more reasonable than the the TJ market. When I decided last year to get into the 4-wheeling scene I was initially looking at XJs because I've had a few in the past, but the wife insisted on a TJ because she likes the whole no top no doors thing. So, I paid 9.5k for a TJ whereas the comparable XJ market at the time was a few grand less.

Yes, the XJ will always be cheaper than the Wrangler being as though the Wrangler is really the iconic Jeep.
 
I've owned 3 XJ's. The first was 4 dr. Laredo that I bought new in 1990. The second was a 1995 2 dr. base model. My current one is a 1989 2 dr. Limited that I drive almost daily. I like the early body style (1984-1996) and in particular the RENIX years (1987-1990). They're pretty basic vehicles that are easy to work on and modify to your liking, or not at all. Parts are plentiful, new and used, and like most Jeeps have a good community of enthusiasts. There's a lot to like!

My current XJ ...

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That is really a nice looking XJ. I would love to buy one like that someday!
 
That is really a nice looking XJ. I would love to buy one like that someday!
Thanks. This one is a Limited. I went from a basic power nothing to power everything. I wasn't sure about it at first thinking that I was just getting a lot of things that would break down. So far so good. The only thing that doesn't work is the power antenna which I can live with.

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Late on the reply here by months, but this is actually applicable to me. My first vehicle at 16 was a 1992 XJ Laredo. That thing ran for years and years and years. If it was a 4wd I would probably still have it over 20 years later. It survived an inexperienced teenager, multiple accidents (totaled twice, once was my fault once not), and only had the engine rebuilt once. When I moved on my Mom drove it for years afterwards. I still miss the XJ to this day, and of course the 4.0.