Re: Painting over existing gel coat
My thought process is to sand the existing gelcoat on my Checkmate, and roll with white gelcoat.
Sounds like it should work. Not sure about color coverage, but gelcoat's pretty thick stuff.
You do need to be aware gelcoat isn't a paint, it's fiberglass resin with pigment and extra weather resistant stabilizers mixed in. You can spray it or roll & tip it, but there's a limit to the total thickness you should end up with, old and new combined.
You would be wise to do some online research. Check out the prep and application instructions for a couple of brands. Even see if there's more detailed instructions at the website of the brand you are considering. Quite often the instructions on the can are the short version of a better instruction sheet the manufacturer has available.
Just like paint, your prep-work will be the most important step to a lasting job. The application work will be for the cosmetic appearance.
Last time I bought from Jamestown Distributors they were putting together a nice How To section. There are also some good DVD videos out for spraying, since that's a little tricky to do.
Look too at the gelcoat suppliers online. I've seen some starting to offer guide books that would probably be good to have handy.