I would say it depends on the paint. Some of the polymer paints will just add a layer of veneer that will gum up sandpapaer and add to the fairling agony. But a light power layer of something like Krylon shouldn't be too much of a bother and a big grit paper like 60 will just annihilate it right away so that you can get on with the rest of it.
Personally, I did color contrasts by different mixes of fairing additives to provide slight variations of coloring. On the other hand, my boat isn't that fair!!
