The real concern I have is what happens to the line where it passes through the sheave of the block, either at the mooring buoy or at the dock. The wind and wave motion of the boat will probably cause the line to chafe, even with the block, and there's really no good way to put any sort of chafe protection on the rope in a block.
I think a dinghy would probably be safer. If you don't want to have to carry the dinghy on the boat... tie it to the mooring while you're out sailing... and then when you've tied back up to the mooring, untie the dinghy and use it to get back to the dock.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.