2012 Jeep Wrangler Sport 2dr SUV 4WD (3.6L 6cyl 6M)
I call this "the last car" because I will never drive anything else. That said, it is not a "car" as much as a street legal toy. A giant go-cart. The feeling of driving a jeep is incomparable, but certainly not for everyone. In fact, if you even have to debate whether you should; then you probably shouldn't. If you are comfortable, however, with the idea of changing a heavy stubborn top (hard or soft), having little freeway acceleration, and generally driving a giant go-cart; then this is the car for you! You have to be prepared to think of your Jeep as a street-legal toy to really appreciate it. (Also, get the manual transmission or just get yourself a minivan)
Off-road ability (duh). Convertible top. Reliability. Sense of freedom and adventure every time you drive. It really is an experience.
None that I can think of. There again, if you know what you are getting into, then you really can't complain about the downsides of jeep ownership.