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The rust on my car is completely hidden and does not go into the fender area at all. It is covered by the gasket. The rust is in the metal part that the gasket goes over. I happen to pull a window because I had water leaking in and figured that was the most likely source.
I suggest pulling the windows and repairing any rust damage first, then paint with the windows and gaskets out.
I use plastic trim tools for all kinds of stuff and they are quite necessary for working with the gaskets, with them you damage nothing.
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