@694spd
Did you ever get things right or even better than your last photos?
I have the same issue in my 67 Dart convertible drivers side (drivers side rear quarter hit and bondo-ed in the 60s, hit and reskinned in the 80s ) my glass will rock in and out of the vent window when all the way up so I might have broken slide there. my vent window assy is parallel to the A pillar trim and quite close. My door hinges are warn ( can lift up whe door is slightly open. have replacements and will do that first)
thoughts anyone!