I wanted to reply to this thread a couple hours ago but I was in class and the response was to long to be typing away on my Droid, so here it goes.
Had a '97 Dakota Sport from new until '08. Great little pick-up, replaced the passenger side ball joints, A/C condenser and that was it as far as any "major" repairs. Had a leak on driver side door, probably due to the weatherstripping being torn up while trying to unlock the car with a coat hanger because of locked keys inside, there was also a leak on the back window but was repaired under warranty. Not sure about final mileage.
My mom traded in the Dakota for an '08 Sebring Convertible. What a piece of [censored] it is. Shift lock actuator snapped, the convertible bucket bracket broke, the rear driver side window stopped going down randomly then randomly started working again, the automatically dimming mirror stopped working randomly then started again randomly yet again, the driver side door catches on something when it closes and snaps and pops shut, thought I had isolated the problem and replaced the lower hinge and guess what, that wasn't the fix. She bought it in IL and then moved to GTMO 1 month later for work and Chrysler voided the warranty because it moved overseas even though if she had purchased the car in GTMO through the NEX Auto Sales it would be covered. Sebring currently has roughly 20k miles.
I had an '04 Ram 1500 was great, nothing wrong with it. Did the usual ball joint replacements that is often done on 1500s and then I had to replace the window washer fluid pump. Other than that, it was great, other than the 4.7l V8 being sludge prone. I know 440Mag will refute this claim. Sold the 1500 with 46k miles.
Now I've got an '07 Charger and other than the 3.5l being a bit of an oil burner I've got no issues. I'm very happy with it. Has 39k miles on it.
My girlfriend has an '04 Ram 1500 with the 5.7l V8 and it doesn't appear to have any issues. She bought it used, well her parents bought it for her, it has 5 previous owners which made me weary right off the bat when she told me but I checked it out a little and doesn't have any major issues. Has warped front rotors that need to be replaced and a squeak on the front end but I can't seem to locate what it is. The ball joints look good, but I haven't gotten underneath to see if it is a control arm or something else, it does it at low speeds like going through a parking lot but not elsewhere. Could be related to rotors but I haven't checked. Ram has 86k miles on it.
The point of all this is that it definitely seems as though Chrysler has gotten progressively worse as far as reliability, hopefully with the Fiat investment they will whip themselves into shape and get back on the ball. I'd love a new Charger when I get out of college but I don't think I could bring myself to buy a new Chrysler product other than a Ram until I know for certain that they've gotten their reliability woes under control.