If you're going to be re-barrier coating the boat, you really should remove all the paint IMHO.
The through-hulls should only be painted if they're Marelon. If they're bronze, leave them unpainted.
Replace the soft filler material with either glass or thickened epoxy.
Foam-rubber sanding blocks are good for the leading/trailing edges of the keel, rudder and hull.
Bad prep is usually the reason for paint flaking. Either the surface wasn't cleaned properly or the paint that was on it was incompatible with the new paint and should have been removed.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.