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Thanks and will let you know how it goes. So, if I paint the inside (under the tire), and the outside, is that overkill?
Yes, because technically, you want the "sealant", in this case the paint, to be pushing into to the "void", by the air pressure, thus filling it, rather than trying to seal against the pressure, if it was painted on the outside.
My recommendation would be to use a product called GE Glyptal, if it's still available.