thanks all for the replies, a followup question.
Hellosalior mentions Stress-relieve it Can anyone expand on this?
I have not yet made up my mind weither to go with the gland deck fitting or a barrel type connection, my local marine store has both. The barrel type connection is a little different than what SD suggests in that it has a plate, about 1 inch in diameter for better deck mounting. With that said I like the idea of the gland. My thought is to use the gland with a one foot piece of cable, connectors at either end. The idea being that if I happen to step on it and damage the 1 foot cable it would be easy enough to replace. With that said I have a thru deck 4 pin electrical connection at the base of the mast that has survived 30 years with out damage so perhaps I am over thinking things a bit.
Regardless thanks for the input, I am looking forward to the snow disappearing so I can get to work.