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After many years of chipping small bits of gelcoat, creating fractures and otherwise manifesting poor workmanship, I have finally reached the conclusion that really don't know what I'm doing.
Ok. That admitted, (I'm embarrassed to ask) how do you drill a small hole in fiberglass/gelcoat, about the size necessary to install a No. 8 or 10 screw, without damaging the gelcoat surface that immediately surrounds the hole?
Carefully :)
If you relieve the gelcoat with a larger bit or countersink it should not crack. Also be sure of the pilot hole size and the screw. If you push too large a screw in the pilot hole it will cause cracking.
As per previous comment, it is important to drill the correct size hole for the size screw you'll be using. It is a common error to drill too small of a hole. I would use a 'brad point' drill bit. A 'brad point' bit has extra cutters at the outside edge of the hole diameter which will score the outside edge of the hole, just before the boring-cutters engage the fiberglass.
Use a new drill bit if possible. Brad-point bits are available at most Home Centers, catalogs or wood worker's hardwares, such as Rockler's. I bought a set of 8 at Home D's for about $10.00.