I carried out a sea trial of the idea.. Unfortunately, it doesn't work. Used a two person inflatable canoe, which is lighter than the fibreglass one in Croesor, but a similar size. The painter was some old 10mm caving rope. The ring was steel, about the same diameter that a carabiner is long. The pull cord was the common blue polypropylene string.
The ring used, with a snap krab as comparison.
The bow to stern painter set up long, with the ring in the middle roughly. I tried it like this and with a much shorter painter. Both behaved the same.
The result.
The ring does not slide along the painter as hoped at all, but remains in the same place. No reversal is going to happen.
Back to the drawing board. Better found out in the sunshine on a bank holiday Monday than underground in deep cold water. The inflatable canoe is as close a substitute to the green fibreglass one as I could manage. I don't think the other boat will be different enough to behave as hoped, despite the extra weight and drawing a bit more when empty.