Jacamo, Not a bad idea to hide the wiring. A 1/2 inch hole through the middle of the post shouldn't compromise the integrity at all. I know you mentioned the exit at the top just below the trim ring, but also keep in mind the exit at the base. You kind can and kinda cant really bring the wires directly out of the bottom of the post, you'll have to come out of the side like you do at the top. The glass it sits on is mostly a cover for the inner liner to rest on the actual keel trunk that is a separate piece, plus directly under the post is the 2x4 the stiffens the compression post.... a whole pandora's box of issues there. Some boats the 2x4 was installed too low or too short or not enough adhesive filler between layers leaving gaps, then the compression post would 'sink', leaks caused posted to rot... the list goes on.
Needless to say you will probably want to come out of the lower side of the post facing port, but you can actually come out of the post facing forward as long as you put an equal hole through the bulkhead that it screws to... BUT, (and I'm not at home to check) you only want to do that if the exit point is UNDER the teak support rail that holds up the panel over the porta potty area. Otherwise you'll have a pinched wire or have to route a groove in it. That's kinda the way my wire routing works, but I replaced the wood with a stainless post and the exit is definitely under that rail. I could have gone straight down into the port lazzarette but at the moment I'm not sure why I didn't, other than the fact that a hole was already there from the P.O. On the forward face of the liner I do go back into the stowage area where my wires route into the inside where the need to go out of sight.
Also, you'll need a jack to lightly lift up on the overhead, the post is squeezed in there tight. Rig down goes without saying... but I said it, lol. I had to use lumber to get the jack set properly and actually away from the post, I think a 4x4 cut to around twenty inches need to help the business end of the jack make contact with the overhead. Also lumber under the jack to get it even footing and protect the interior gelcoat.