Roger
I sympathise with you wanting to be 'precious' about your boat, and have similar feelings for my BR20 Halen Y Mor. After two seasons sailng I have not detected this sort of wear on the mast cleats - which look as if it may be caused by friction - ie the halyard running across / round the cleat under a bit of tension? I rarely have cause to do this. If pulling the sail up (by hand), there is no need to have the halyard running through the cleat; if pulling it down, I want as little friction as possible so just hold the loose tail of the halyard in my hand whilst pulling the sail down. If you are using a winch to pull the sail up and are running the halyard through the cleat - this might cause the sort of wear you show?
There is a knack for getting the mainsail all the way to the top of the mast without incurring a hernia: Firstly ensure your halyard is exiting the top of the sail on the same side of the mast as the halyard block (starboard on mine). Secondly try tieing the main halyard off on the lower of the two holes in the head of the mainsail. Thirdly, apply some silicone lubricant spray to he mast track before raising it. Fourthly, double check you have everything else good an loose - reefing lines / down hauls, mainsheet, kicking strap. Fithly, use the cleat to take a turn around as you near the last few inches to 'sweat' the sail up to the very top. Once the sail is up, then tie off to the cleat. I haven't found this to cause noticeable damage to the cleats.
Happy hauling
Gareth Rowlands, GRP BR20 Halen Y Mor