i approach it similar to Dan.

i do a pilot hole with a 1/8 bit. my drill has a level built into it....so i can make a straight hole.

i will check the pilot hole to ensure i got it right and then enlarge it in steps to 3/4 drilling into each side.....and meeting in the middle. to prevent tear out.

then as dan said....fill with epoxy and repeat the above process only to 1/2 of an inch. this gives a nice 1/8 inch of hard epoxy protection around the hole.

this is a bit larger than what dan describe's....but i find it looks fine. could make it smaller...but you can sort out what looks nice to you.

fwiw...i also use some bungee as part of my toggle system....to hold the toggle to the deck.... when you let go of the toggle....the bungee automatically pulls it tights against the deck....so no banging toggles while you paddle.