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I have asked around and cant seem to get a straight answer on what I need to do. I am re-siding my house and all the trim I tore off was stuck on great and it was done with countersunk finish nails and then caulked over, you couldnt see a nail hole. This trim was about 20+ years old with no issues. I have talked to a couple of people and they are all telling my I need to use a nail WITH a head on it for trim. So which is it? And does it really even matter? I think a headless counter sunk nail would look better close up.

I was thinking I should use an 8d nails as well, is this correct?
 

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finishing nails on trim. 8 is probably fine, if sufficiently long to get a solid piece of wood to nail to. even i am not tacky enough to use headed nails on trim.
 

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Drywall contractor
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Finish nails. Might want to go with galvanized to be on the safe side...
 
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