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I'd go with the roller first meng. then tape around the edges of the trimming and such, then paint the trim. Mess up all you want, (provided you don't paint beyond the edge of the tap onto the walls...if you do this you just don't deserve to hold a brush) and finally, remove tape.
viola, sharp, clean edge.
But that's just how I do it. So, really you could do it however works best for you.
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