All boat owners hate to drill holes but in this case it's normal. The bigger issue is that every few years, you need to "unstep" the mast. When you do so, you'll find wires to the mast head, for the anchor light, any radio or Instruments mounted there. You might find foam padding to keep stuff from rattling inside the mast......It's all normal. While your at it, spreaders need a close inspection and every fitting and cable end needs close inspection. Replace the bulb in every light mounted and make sure the wind indicator is in good condition.
Now, having said that, when was this last done on your boat? Ask your boat yard how they unstep mast, and what they charge.....then ask around at other yards. Some do this so often it's no big deal and it's much less expensive. others don't do it much and are not equipped to do it, so they charge a lot more. Once down, you can mount the light yourself or hire a rigger to do it.
I'd plan everything you want to do and do that at the end of the season, (winter) or next spring. Unless there is a pressing need. You need to get to know your boat this year. You might find other things you want to do, like replace a radio antenna......so, I'd wait.