If you pad the pole, you are going to slide the fat part of your topsides against the padding as you work your way in. With 2 kts pushing you against it....I think it will make a mark, even if it doesn't get buggered up from the tide.
I know people who have used the dock wheels. If you could figure out a way to mount one...but I also know people who have hit them hard, burst the tire, and put a hole in their boat.
This is black diamond docking your trying to do