Thanks Rich and Dan for pointing out that my simple solution probably won't look so hot. I will look into the mini sprayer idea, though I'm not very good at or experienced with that finesse finish type of stuff.

I just discovered that Starboard makes a finished circular base; I could get a base slightly larger than the winch diameter and that would hide the old holes. It might not look totally natural but at least will get me by until I decide to tackle the nicer solution.

Thanks again,
Max

PS yes Dan, it is smooth gel coat in that area