My 1 success and 2 relative failures might help someone's decision in favour of a poured rubbery 'mast wedge' solution.
Years ago I stepped the masts with a Devcon 2-pot Shore-80 rubbery goo, poured (with some wood/rubber chunks as volume-fillers) into a big tapered gap (~6cm radially) around each mast. The load distribution and leakproofness were perfect. Success.
I did not use a release surface, Failure #1: I had to saw through 7.5cm of tough stuff with a scary saw to unstep the things. I patched up and rebuilt the system using SikaFlex in a pinch, and they worked practically as well as before. No leaks.
Fewer years ago I duplicated the basic process, but used glass-epoxy instead of rubber to fill the tapered gap, with a release surface - the 'wedge' is part of the mast. Failure #2: The masts creak and move a little, though I thought them immovable, and the mainmast has defeated my carefully-machined-and-prepared SikaFlex-injected gasket idea, which really should have sealed if there were any justice. It took hard sailing to show any problems, as is traditional on boats...
The rubbery products will apparently seal against a release surface well enough the first time, but I'd be suspicious after a second stepping.
So, next time...
Cheers,
Kurt