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Now i know rubbing is racing, but not on my new paint job. My dock cleat is behind the bow of the boat so the lines angle slightly backwards. How can i prevent the paint from wearing through again. This only took 2 years to rub through. I was thinking of moving up to 6 inch chocks and trying to get them somewhat closer to help the rope stay off the toe rail.

i dont know if you like the look but maybe a sampson post instead of the cleats to get the line up off the deck a bit
I actually think it would look better than those 2 old fashioned cleats anyhow

or consider refinishing that area in gelcoat, it will allow a bit more wear and when it does go through again just have it repaired

What would happen if you raised the chock on a piece of teak?

You can add two of those SS guards on the rub area, similar to those you just removed from the pulpit.
Only make sure that the screws are really sunk in, otherwise you'll have the rope rub on the screw heads.