Re: docking alone
For the guy with the O'Day 25, I'd buy a single track mounted cleat first and try it out. I personally found them annoying on my similar Catalina 25, they really liked to grab the genoa sheets when we were out sailing, and then someone would need to go forward to clear them. Trying to shadow the cleat behind a stanchion eliminated most of this, but made it harder to use the cleats. After a few months I stopped using them.
A sub-5000lb 25' boat with an outboard that pivots lets you get away with some things that are a lot harder to do on a larger and heavier boat. It's been a learning experience for me going from a 5000lb Catalina 25 with an outboard to having a 8000lb 29' boat with an inboard. This thread has had some useful tricks.