Rupert, I have no doubt that the Chryslers you've owned have served you well. In fact, my F-I-L swears by the Caravan, he had a second generation one last him until just a couple of years ago when it was trashed after being stolen, though apparently early in it's life, it needed a new tranny under warranty. I believe he got well over 350,000 kms. He now has a fourth generation Caravan, still too young to say anything about the mechanicals, but when new, he brought it in for some trim problems under warranty. Definitely maintenance is a huge part of vehicle longevity. And I don't dispute VW has a spotty reliability record, either. Though I really enjoyed our Mark IV TDI Golf (manual transmission) and that car was reliable, there are other VW products I won't touch with a 10 foot pole. I'm not keen on their gassers, but I could be swayed. Same with their conventional automatics, not keen on them in general, and would avoid certain trannies at all cost. DSG? Scratch that for me. Their TDIs for the most part (save the "PD" engine from '04-'06) paired with a manual transmission make a good combination in my mind. But as a VW owner (I'm like this with all my vehicles, regardless of reputation for reliability), I would be absolutely on top of maintenance, taking a very active role.
So Chryslers and VWs both have questionable reliability (one I think is worse than the other, but I'll leave that for you to decide who I'm referring to), yet we've both been able to find vehicles that buck the trend. Big difference for me? The VWs generally have good driving dynamics, good fit and finish, nice interior appointments, good resale (at least on the TDIs). Can't say any of that for Chrysler, and yes, I've driven many - rentals and courtesy cars (I had a Dodge Colt in my youth, not a true Chrysler), and had many a Neon
as a courtesy car when I took my own car in for service. When I rent, I dread getting a Chrysler because I don't like the way all the ones I've driven in the past feel. So there's the difference in my mind. I would pick almost anything over a Chrysler any day, and that is my personal preference, but I get the feeling I'm not alone in this camp.
I don't believe in being a fanboy or hater of any one make - I would rather judge each car on it's own.