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Feathering.
If it was a dent only on the fender then paint the whole fender, if it was a dent on 2 panels say In a crease, then yes I would paint both panels.
Listen if you dont do it right the first time, dont do it at all, otherwise might end up with your handy work
Ok so prime, then feather out till smooth, then lay in the paint. Anyway it's easier said than done and would like to end our silly ramble. Each of us have a way to do it, I'm sure your skilled and I'm skilled. The end. Anyway Merry Christmas