nails hole are fine....anything larger is not. The wood filler is not hard or rigid enough for a large hole. Especially on a exterior. Change in temperature and moisture causes movement, even though it may be slight if its not a two part compound or a epoxy or something that dries hard and dense-----> pop. Out comes the elmers. Seen it a thousand times on exterior repaints. May not happen right away....but over time it will.
My hardwarestore is selling trim head screws with white pcv caps that you can just put right in the hole after the screw. I have seen samples and you can't even see that there was a screw there with the cap in.
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