The ongoing saga - bowsprit removal with the boat on the cradle and skipper who's afraid of heights.
We managed to get the sprit off by taking all the pieces off first - I hid below and installed a new V-Berth fan while Andrew (who is much braver than I) climbed out the end of the sprit and took off the pulpit and platforms. Both came off really easily and the platforms were rot free. We had an incidental finding of old running light wiring in the pulpit that was an old length of yellow extension cord! The bolts through our fibreglass riser and the sampson posts came out relatively easily as well.
My clever husband wedged our winter ladder under the end of the sprit just aft of the eyeband so when we had it loose, it didn't fall to the ground. It was easy for us just to pull it onto the foredeck then lower it to the ground. Overall, it took about 3 hours to do - then another hour to clean up all the old sealant and spider crap.
It looks like all the bolt holes are nice and dry - I had previously removed the windlass and did what you suggested with its mounting bolts. There was some water in the deck there that had compromised the sampson posts as well. I followed the instructions in Don Casey's book for dealing with that problem, ending up drilling 10 holes in the area forward of the posts and filling with epoxy plus doing as you suggested with the windlass holes. New sampson posts made of white oak rounded out that project.
I'm excited about the welded platform for the windlass on the new SS bowsprit. The wooden blocks are always a place for dog hair and spider nests to collect and I am a really tidy girl so am constantly cleaning! Plus the idea of being able to fill four holes in the deck appeals to me.