#1
Ok well I don't think these were coverd in the ultimate refinishing thread, so here I go.

I'm going to paint the back and front of my guitar while hanging, and then the side while it's layig down, slightly elevated on a block or something. My question is, Do I have to mask the side while I'm painting the front/back, and do I have to mask the front/back while painting the sides?
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#2
Well, You should ideally mask them both off just for ease of use (It's alot better to mask twice than to sand down what you just painted) Remember, there is a thing called overspray, and it sucks. You could probably get away without masking the sides when you paint the top/bottom, but I personally would just spend the little extra time to do it to the extreme.