FWIW, we had a 3.75" dia hole in our
deck when we replaced the
windlass. I taped the bottom (with duct tape!), mixed up some
epoxy and poured the hole full/level. It set up, I sanded/roughed up the top and bottom, repainted, and then cut the new hole for the new
windlass...and installed it. That was 5 years ago-no issues or problems; solid and strong-and no
wood to delaminate and/or swell if/when it gets wet. Easy and simple!