Transmission hard shift - FIXED!
Well after a year plus of the random sip and slam into second gear and lots of useless visits to the dealer and Chrysler Care communications, it's finally fixed.
They changed out the whole transmission and I've driven 1,400 miles so far with no issue.
The key was the "check engine" light finally came on and there was an error stored that the dealer could see (they always would say if it doesn't happen on a test drive, or there is no saved code - they can't do anything) The code showed a problem with a "speed sensor" but the dealer was advised by corporate, to swap out the whole transmission. It's suspected that corp knows there is an issue and wants the whole thing to study.
Here's a hint to maybe help you get to the point of it finally erroring out... It happened when my birder wife was driving on a bird count. That means it was driven very slow with stops and starts for a couple of hrs.
Anyway, I'm glad that it finally seems to be fixed. I really love this vehicle, but that sure was frustrating..