How do I mask a checkerboard pattern?
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If you're talking about masking for painting, it has to be done in 2 steps. Mask for the verticals and paint, then mask for the horizontals and paint. Do the darker color first. Light colors cover better than dark colors, usually. If you're literally painting black and white, I would paint the white first.
Since you'll be masking relatively fresh paint (unless you wait a month), make sure you have good adhesion so that the masking doesn't pulls off the 1st coat.
I recently tried Frog tape. It worked extremely well so it's not all just marketing hype. It sticks pretty good too so it can easily pull off poorly adhered paint.
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Found more instructions at This Old House (which I rarely consult):
http://www.thisoldhouse.com/toh/how-to/overview/0,,20312013,00.html
My way seems easier.