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My house has very old siding in rough condition as well as an assortment of fixes / replacements to rotted sections of trim. We have improved the siding condition and filled in and fixed holes to the extent afforded in the budget. There is still a fair bit to cover up here: it is about 3500sqft of exterior surface to paint. I am however leaning towards a Satin finish due to better protection from the elements.

What are some considerations for reducing the obviousness of the imperfections given that a [semi-]gloss finish apparently does tend to bring them out into more relief?

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  • Fill with external filler, sand then paint.
    – Solar Mike
    May 22 at 17:23

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For larger imperfections, actual filler/putty. For smaller ones, and after the filler/putty step, use several coats of a high-build primer and sand it back to flat (not sanding it "off" just sand enough to level the surface, where the primer will have filled in the smaller imperfections.)

This is considerable work, but as always with paint, 90+% of a good paint job is the prep work.

If it makes you reconsider the choice of paint finish, it will at least be a more informed choice. If you're willing to go through the agony, you can make it look good. It might not be worth that agony, though.

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