"There are only two colors to paint a boat--black and white, and only a fool would paint a boat black"

Nathaniel Herreshoff

Now, I have to disagree with Cap'n Nat. A dark colored hull on a classic boat looks striking. But, its harder to achieve and maintain a nice finish.


Getting back to the project, I'd probably approach it like this:

Take off the metal rubrails

Clean the area with a degreaser like Formula 409

Wipe with acetone

Sand out the loose bits (save the largest paint chips) bevel the edges

Get the dust out, wipe with acetone

Mix filler thoroughly

Trowel it in using narrow and wide plastic scrapers

Wait a day and sand, sand the corner by hand

Reapply as needed