[Viffermike]

OP, I drove a friend's 500 Sport from Dallas to San Francisco a couple of years back. It was great fun -- the engine can take quite a bit of abuse: though it doesn't sound like it wants to rev, it will ... and you'll need to), and I didn't have a single issue on the trip save for running out of gas on I-20 just east of Abilene (A guy named Jim Bob -- no foolin' -- gave me a ride to the service station.)

It's a defensible choice for towns like SF because of its size and style, as well as because it's relatively cheap to run and fairly roomy in the front seats. All that said, the 500 is one of the least-reliable cars on the market. It's built just above the quality standards of a tin can. It's paint is horrible. Its badging is known to fade after 2-3 years. Its audio system is roughly on par with My First Sony in quality. Its switchgear and interior bits are made from plastic that's more suited for a model airplane kit than a car interior. And oh. My. GAWD it rattles.

There are better choices. Mine at that price point would be a Chevy Sonic hatchback. Those are fun little runabouts. Reliability is much better, as is build quality. You can easily find a 2-3-year-old LTZ (top-line) for under 10k. If I move to a colder climate (somewhat likely in the next year), I may very well get one myself as a winter beater second car.