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Think similar materials.
oil sealer + oil primer + oil paint + oil finish coat and you'll have compatibility and better adhesion between coats.
it takes a long time for linseed oil to be dry enough to paint over, I don't like it anymore.
The belly hole is your obvious entry point for water to begin to expand the wood. Poplar will soak it up like a sponge and expand , then it all fails .
try some val oil or tung oil maybe as a sealer and use a better primer
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