Is the gap between the rubber seal and the front glass? And is the door glass tipped outward relative to the rubber seal?
If the rubber seal doesn't meet the door glass, the adjustment is likly needed at the rear window track.
Both the door glass and rear window can be adjusted slightly from within the door or body space. You would need to remove the interior panels to get to the adjustments. Rear windows not rolling up and down are likely the result of the rollers either worn, gunked up, or broken. New rollers are relatively cheap, but they are a PITA to get in. But they make the windows go up and down like new.
I used to be indecisive. Now I'm not sure. I feel like I am diagonally parked in a parallel universe. 1968 400 convertible (Scarlet) 1976 T/A - 455 LE (No Burt) 1976 T/A New baby, starting full restoration. 1968 350 - 4 speed 'vert - 400 clone (the Beast!) 1968 350 convertible - Wife's car now- 400 clone (Aleutian Blue) (Blue Angel) 2008 Durango - DD 2008 GXP - New one from NH is AWESOME! 2017 Durango Citadel - Modern is nice! HEMI is amazing! 1998 Silverado Z71 - Father-daughter project 1968 400 coupe - R/A clone (Blue Pearl) (sold) 1967 326 convertible - Sold 1980 T/A SE Bandit - Sold