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My experience with vinyl tops is this, they hold moisture and the metal underneath will rust. For me, they are too much trouble. If you want to restore the car fully then I can understand your desire to do the vinyl top as well. I would recommend using POR rust converter, it is a heavy black chemical coating similar to primer, you don't have to remove all the rust and in fact they recommend that you dont. I think that what you are asking though is how to apply any kind of treatment without it dripping through the hole and onto the top side of the headliner. I don't have an answer for that. Maybe stuffing some kind of absorbant cloth or paper material into the holes first...? If you find a way to do that then using the POR product would be my recommended first step followed up with an epoxy type body filler and topped off with a good primer before you apply the adhesive and vinyl. Hmmmmmm, I just thought of some of that expanding foam insulation stuff, if you are very careful you might be able to squirt a very small amount into the holes just enough to prevent dripping, maybe try on a scarp piece of metal with holes of similar diameter first to see if the foam will adhere to the hole and fill it without dropping off the bottom......Just brainstorming here, none of these ideas may work but good luck. If you do use the expanding foam, check to see that the POR product does not eat it away, that would be bad.
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Dan
'77 Cutlass Supreme
'46 2 door
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