Its funny, I had a conversation about this subject with Dudley Dix last week. I had mentioned my idea of creating a moment connection at the deck so that I had a deck stepped mast that behaved like a keel stepped mast. He told me that he had used the balloon and epoxy trick very successfully on one of his boats. While that does not solve the issue of being able to jetison a lost mast at sea before it holed the boat, it at least stopped the water coming down the mast.
To avoid the issue that SD raised, if foam is used, it needs to be a closed cell foam so that it does not tap moisture against the mast. (Not all spray foams are open cell.)
I have watched for leaks around my mast boot, even when I try hosing it at full power, and it generally does not leak. I typically loosen the clamp and boot and recaulk it with silicone every couple years and as a result leaking at the boot has not been a problem.
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay