>the fiberglass right at the edge of the hole looks like it
> gets "starred" or lifted a bit.

You mean delaminated.

Next time put a piece of masking tape over the area you want to drill first and then drill through the tape.

> Should I fix this somehow?

You could probably put a little resin over it or inject the edge of the hole with resin if it's between the plies. I'm guessing it's not too big of a problem on a kayak. It would be a big problem on airplanes. Moisture would get in there and freeze at altitude. Freezing water expands causing more delamination. When the plane comes down more water goes in.. and so on... and so on.

>Does this mean that the fiberglass on the
> entire boat is not really adhering too well?

No

Dale