My experience: When my boat was 1 yr old, I decided to keep it in a wet slip and so I had the bottom prepared and a barrier coat applied, then 2 coats of whatever Interlux' best ablative paint available in 1992. It lasted 7 yrs with the boat in the fresh/brackish water of the delta.
I pulled the boat 3 times each summer to high pressure wash the bottom, transom and outdrive. Also, I discovered that by running my boat into salt water for about an hour on plane, the bottom got really clean.
Brian, I'd suggest you run the boat into salt water if possible, then haul and power wash it while it is still wet before putting it away for the winter. You might be able to go longer between painting that way. Also keeping the boat on an air dock during the summer might turn out to be cheaper then doing the bottom paint thing every year........in the winter you can deflate, clean and store the air dock.
Good luck!
Then I got myself the air dock and have never bothered to repaint the bottom