Unlike this picture, I prefer not to paint boards. It does save work to be able to leave the board(s) floating at neutral, but as I see it the trade-off is against you.
In my experience every board will get damaged. Even a gravel bank will scuff it up some. A reef will do even more. Doing the sanding for repairs on a board can be poisonous. I killed the lawn for several years where I sanded the tip of my rudder once. Throw a halyard on the board(s) and pull up until its out. You will be appreciated by your future self.