My first guess is that the 1-3/16" gap up by the wing window is your first problem. Underneath the wing window there are two metal tabs that are welded to eachother. On tab is tied to the inner shell, the other is tied to the outer door skin. On my doors, as well as a parts door, the tab had broken away. I beleive this is the only piece that ties the two panels to eachother along the top. 1-1/16" is about what I measured befro I replaced my door skins. If you want to inspect the tabs, remove the inner door panel, and you should be able to see the tabs beneath the bottom of the wing window.
As far as sealing up the glass to the weatherstrip, the glass should have the proper seals installed. If the glass was ever replaced using the original glass base but with generic glass setting tape, then that could be cause for some leakage.
Here's a link to another post that shows what the window seals should look like on a'65 El Camino door...
http://www.chevelles.com/forums/showthread.php?t=211700
As far as sealing up the glass to the weatherstrip, the glass should have the proper seals installed. If the glass was ever replaced using the original glass base but with generic glass setting tape, then that could be cause for some leakage.
Here's a link to another post that shows what the window seals should look like on a'65 El Camino door...
http://www.chevelles.com/forums/showthread.php?t=211700