So the latest is the passenger side regulator decided to self destruct. Pulled the window and regulator, since I'm not going to be driving it until that side is put back together I decided to look into why the drivers side window is not seating well against the belt weatherstrip along the top of the door. There was a gap outside and the window seemed to be pressing tighter against the inside.
Pulled the window and compared it to the passenger side. Drivers side has much less curve to it and would explain the fitment issue.

Edit: I think the drivers side glass is from an SLK. It's marked Pilkington, all the slk glass I found online are Pilkington.
All the Crossfire glass I've found online are Safelite with the Chrysler logo as is my passenger side window.
If this really is the case then Slk glass fits but not quite right.