Mask is down and it's time to repaint and reseal. After removing all the hardware what would you use as a temporary filing for the holes? It will take me a few day to clean, sand and repair deck. I don't want to get caught in the rain.
That's what I did - push butyl into the holes, mound it up a bit - so water sheds off, and cover with duct tape. It's kept the holes in the deck dry so far.
Run a slightly larger drill bit through the holes. Bevel the holes with a countersink bit, tape them from below, and fill them with thin epoxy. When you're done painting, re-drill with the proper size bit. The wood in the holes will now be (theoretically) impervious to water intrusion, even if the bedding fails.
It'll add a day or two to the project, but ... as long as you already have all the hardware removed ...
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