I start with the boot inverted, pointed up and lay a bead of goo under the raw edge before I start frapping it with twine from above the goo line down. So the squeeze out just pushes down. Once the boot is flipped in place the frapping and any squeezed out goo is hidden under the boot.
Of course you need some sort of raised ring or collar at the deck level for the boot to be frapped tightly to at its bottom.
Takes a little dry fitting to be sure you've got everything aimed right.
Shoe goo does not adhere all that well to the paint I use on my mast and I don't move the boot unless it's gotten old and tatty anyway. I've not had a proper boot last less than ten years. No problem painting above the boot or below when needed, and just leave the boot attached to the mast all the time.
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