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I drove an 05 unlimited wrangler through my soph-senior year of college. It was my first car, and I just graduated and sold it.
Pros-
Fun to drive if you live in a nice area - I am in AZ so it's no roof for 8 months a year.
You can go almost anywhere offroad with stock setup
Timeless looks and a good "cult" community
Lots of mods available for used and new. It's like "lego" car, great if you're into creativity.
Unmatched resale value
Relatively safe, I got rear ended while I was stopped, the guy clipped my drivers side rear at 65 mph. I didn't feel a thing expect, my wallet did though.
Cons-
Had to spend 800-1000 on repairs every year I had it.
Loud on the highway/ uncomfortable for long trips (have a softop, JK models with hardtop is probably a huge improvement)
Slow, and underpowered. Hard to pass people, terribly slow going up mountains.
My 05 felt about 10 years behind when it came to comfort. My roommate had a 97 and it was practically identical. hand-rollup windows, plain interior, bad stock sound system etc.
Long post but I will answer your questions directly:
Is there anyone driving JW as a daily driver? I did, and never will again.
How's the reliability? God awful. Constantly broke down. However it's popular and domestic, so it's cheap. Easy DIY repairing as well.
Is it cheap to mod? - I don't plan to mod anything off road related. Only purely cosmetics like the picture above. Yes, there are a lot of Jeep owners. This means a lot of used parts available.
How much discount can I expect when purchasing it? Can't speak directly from experience on this. However, they are always popular cars and thus dealers don't have problems selling. I wouldn't expect much of a discount.
My PERSONAL opinion:
Cayman. Or another truck such as a Ford F150, Toyota Tacoma, or Toyota 4Runner. Maybe go for an older model year on a F150, and but an old TJ wrangler to keep for the weekend trips (if you are an outdoorsy person)
Sorry if this sounded negative, but I strongly believe Jeep Wranglers should be reserved for a "toy car" that you take off-roading and crawling. They aren't even good in the snow, because of the top heavy design.
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