Depending on where you're from, the answer to what most people are looking for can change.
As someone who lives on Long Island, I can tell you that specific to the island, TJs (97-06) & JKs (07-16) are what the average, prius driving, starbucks drinking person thinks of as "a jeep." That's my personal experience - people see the square headlights of a YJ (87-95) and don't even know if it's a wrangler or not. I've even had people ask me "what is that?" any worst of all - No return waves from a single JK owner.
That said, TJs on long island typically range from $7,000 all the way up to $14,000. Depending on mileage, rust/rot, engine/transmission combos, mods, etc.
JKs I've seen on craigslist for anywhere from $19,000 to the mid $30,000 and these are all with 20 to 30k on them already - you can buy a new JK Sport for $22,000 I believe? I digress.
You'll get different answers depending on the person, but I enjoy my YJ. I got lucky, mine is a '95 with 105k, came from California, no rust anywhere on the frame or tub. I paid $5,000. Compare this to the prices for YJs & TJs in Upstate New York, where they go for $3000 - $6,000 with around 100k on them.
You're probably wondering which engine & transmission combo to go with? If you're looking at YJs or TJs the 2.5 & the 4.0 are practically brothers, AMC lopped off two cylinders from the 4.0 Inline 6 to create the 2.5 Inline 4. Both have been known to go for 200-300k and you can find owners of each engine on the forums with 300k on their stock engine. IIRC there was a 2.5 owner with 375k on his engine. Obviously, if you take care of it, it will take care of you.
Transmissions is where there is a difference. I can't say much here, because I don't know much about transmissions, but the AX-5, which came with the 2.5 4 cylinder, is known to be very delicate. The AX-15, which came with the 4.0 6 cylinder is stronger.
In the end, it's your choice. There is a YJ owner on here who found a jeep parked in a garage, with I believe 31k on it. The YJs are quite easy to work on, in my experience they're a windy, bumpy ride, and you're not going to win any races, but it's not a Mustang, Camaro, or Corvette. I'm partial to the YJs because I own one, it's my first jeep, and I like simple things - IE no A/C, no courtesy lights, no heated seats, you get the idea. There's so much that could be said for all the different model years that it's hard to summarize all the pluses & minuses in so few words.
To close, if you are mechanically inclined, go for the YJ or TJ. In my personal experience, I've learned more about cars in the past year thanks to my YJ than I would have tinkering with my Mustang. If you want the experience of learning about cars, the older Jeeps will teach you that. You'll end up customizing whatever model you decide on so much that it'll become specific to you as a person. Just as an example, in the 8 months I've owned my jeep I've spent over $1,000 on it, all to make it fit my likes. I'm holding a build list 2 pages in length, things like LED gauge lights, new seats, new distributor cap, ignition coil, new exhaust system, you get the idea - your jeep will be YOUR jeep right down to the floor mats you put in.
If you provide some feedback as to what your intentions are for a jeep, we can definitely help you. Say you want to go offroading? We can help. Say you want to drive it on the street? We can help. Say you want a DD or a weekend driver? We've got you.
P.S. Autozone sells Jeep logo floor mats & steering wheel covers for a good price. Nice place to start customizing.
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