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Too Short? Cut it Again!
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I try not to use tape unless I have to do so or there are to be many coats. I have been pleased with frog tape. It is supposed to have some patented edge system that seems to keep paint from crawling underneath. I always take a drywall knife and burnish tape down.

Oh well, you will find with a quality trim brush and some practice you will become more confident skipping tape for exactly the reasons you suggest.

By the way, I usually prefer to paint trim first and cut the wall color into it.
 
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