I bought my Wrangler in 2008, so it was 8 years old for $9k. JK's had only been out for one year at the time, so it was a great deal at the time. Their prices do seem a bit absurd today. The good news is that mine has actually gained in value since I bought it, as it is a lot better now than then.
What it looked like when I bought it, it had 102k miles, and now has about 135k miles:
My father in law was looking for one like he rode in Vietnam when he manned the 50 cal on it. I was finding rusted garbage for $4k. Finally found one from a former military guy in KS and got them in touch. He got his for $7,500 and paid to have it hauled here because the top speed is 55 mph and he has no top. I think it has 40,000 miles on it because the guy drove it to a military base as a commuter on nice days.
It didn't come with the 50 cal installed though.
TJ Unlimiteds will go up in price. TJs too. It's the nature of cars. Ours get abused so much they'll go up sooner.