Use a drill press for drilling fins, no exceptions. Sure, you might get 'er done with a handheld, but you’re just as likely to ruin the fin you spent so much time laying up, cutting, and foiling. If you don’t have a drill press, ask around. School workshops, neighbors, car mechanics, they’re pretty common.
Stainless Steel “roll pins” are available at most ACE hardward stores in the little pull-out bins. 5/32" is a good size to match the slot in a finbox. It should be 5/8" long, so it sticks out 1/8" on each side. My ACE only sells them in 1", but just clamp it in a vice with 3/8" sticking out and you can run your hacksaw blade right along the side of the vice for a straight cut.
Center the hole 1/4" up from the bottom of the fin’s base (which should be 7/8" tall x 3/8" thick) and 5/16" in from the end. Drill the hole at the same 5/32" as the pin, no need for a tight fit. Put a dab of 5 minute epoxy in the hole right before you tap in the pin and it will stay.
For the screw hole in the tab, the danger is in splitting the glass panel as you drill. The bond between layers is much weaker than you think, when you’ve got a drill bit burrowing in. The path of least resistance is not to remove material, but to just crack open and then you’ve basically made yourself a glass on.
I take 2 blocks of hardwood, at least 2" square and exactly 7/8" thick. I clamp the tab tight between the 2 blocks. The blocks being the same thickness as the fin base means that I’ve now got a 4 3/8" wide base sitting in my drill press, not a wobbly fin. This ensures that the hole will be plumb (90*). Even more important, the wood blocks won’t let the glass tab crack open, which means the drill bit actually will remove material like you want it to. I also clamp the whole thing (blocks, fin, and horizontal clamp) down to the drill press base, so the work doesn’t lift up along the bit as it turns. Take your time, do it right.
Edit: I always make fins with the screw tab on the front. Lots of reasons: (1) I can actually drill them out as described above; (2) I can slide the fin all the way to the back of the box, which I seem to want to do way more often than I want to slide it all the way to the front; (3) If you hit a rock, the tab or the screw plate (especially the black plastic ones with an insert) will likely fail and your box / board will be preserved; (4) if you want to, you can tighten up the fit of your fin with some clear fingernail polish and skip the front screw altogether. This makes the fin adjustable out in the water, and definitely protects your box if you’re surfing over shallow rocks and are likely to hit stuff (not recommended in heavy kelp). If you hit something, you don’t lose the fin since the roll pin holds it in the back of the box. I do this all the time…