So, they say no plan survives contact with the enemy, and most don't survive contact with reality.
My first problem was one of light, and temperature. Unfortunately after I got away from work, bought the appropriate things and got out to the boat, I didn't have alot of spare light to work in. Also the temperature was falling and I needed enough time for it to partially cure before it dropped below 10.
So I simply set about preparing both the screw holes. It was at this point I discovered problem number 2. There are multiple screws that, while not anywhere near as bad, some have lost their grip on reality or at least on my boat.
This leaves me with a dilemma. Do I remove the rub rails completely?
I'm thinking probably yes, they are in desperate need of some sanding and oiling and general TLC. However this presents me with two problems. 1: there is no way I can get them ashore from my mooring without getting them wet and 2: I can't put them in the car to take home.
So for tomorrow I plan to repair the original two holes - they are the ones most in need. After that will come up with a plan of attack for the rub rails.
Did get to see a nice sunset though: