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.
Heading back to Lake Ontario for this summer. Now in Bermuda and heading to Long Island Sound in the first week in May. Then on to the Hudson and the Erie Canal.