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.......... How do you guys suggest I go about this? I don't want to get black overspray all over the nice white paint job, but masking it will be too sharp of a line. Should I just use a brush with some flat black enamel over the white? I imagine spray paint would have too much pressure to avoid the overspray....
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Use a method referred to as backwards masking where the edge of the masking tap is bend back towards itself (no folded!!!!!)
This produces a soft edge rather than the sharp edge like you see on cars above. Paper/mask off the area above (also mask off the front fender edge if the fender is installed) and shot the pinch weld and bottom of the rocker panel with a can of semi-gloss black (rattle can) pressure will be a minimum and you will not get any overspray if you paper the area and point the nozzle the right direction
Seen owners do this on the show field and in the parking lot - you can do it