Jeep Wranglers hold their value extremely well. If you’re wanting a newer one, stick with the 2012’s and up. They have the newer, and better, 3.6 engine. The 2007-2011’s have the 3.8, and they don’t have the power for the jeep.
I drive a 2005, which has the old reliable 4.0.
I have a 2004 with the 4.0. I love Jeeps, but they do have their quirks. Mine has a leak somewhere around the back window, smells all musty when it gets wet, like now. Transmission slips a little, I think that's common for that year. Blower only works on high (just haven't gotten around to fixing it, think it's probably the resistor, another known issue, cheap fix), etc. Mine is the Columbia package, i guess that makes it slightly worth more? Developing some rust that i haven't decided what to do with.
It suits my lifestyle. We took the back seat out to make more room for groceries, dogs, etc. I love just getting in my vehicle and going in the winter, no shoveling snow. The short wheel base makes them super-easy to park, too.