I would run the wire up high along the inside transom. Install an 8'' Beckson Deck plate in the center of the inside transom. This will give you access not only to this wire, but the gudgions, the self bailing cockpit hose, your swim ladder, and your stern light.
I use my access plate twice a year when I run my outboard charging wire to a term board which I have located on the rear Port bulkhead just under the lazarett cover. I had changed this charging wire over to a #10 copper stranded duplex wire and I have another one just like it going from the term board to the battery. It's a better connection than any electric outlet plug and socket I've used in the past.
At any rate, access deck plates is the way to go. I installed a 4" Beckson in my fuel locker so I could get at a jam cleat I wanted to install for my furler control line on the Starboard combing. I can even get at the stern cleat now if I have to.