I also have a Hood mast of similar size (a bit smaller I guess). Interesting that my mast wires come out just a few inches above the end of the mast under the cabin sole level. This keeps them out of the way at least, if not easily accessible. I wonder if it was a choice by the boat manufacturer to do it one way or another?
As for your question, I would imagine it depends on how large a hole you are thinking about. All my wires come out of one hole that it about 1.5" in diameter. Gives no accessibility to the inside of the mast at all. I am taking my mast down in a couple of months to replace all of the wiring and to add extra attachments to the conduit since a couple of the pop rivets have come loose. I will have to consider the hole question, but I don't imagine I will change it. BTW, the Hood masts are great, heavily-built pieces of kit - I imagine could take a lot of abuse with hole drilling.
Finished the circumnavigation in early February in Grenada. Have to work on a book project for the next several months so the boat will be waiting for next year.