If the toerail is only cosmetic...then screwing into the fiberglass toerail is probably going to work fairly well. I would still bed it like hardware and countersink the holes. Last thing you want is a row of drips all along the side of the boat.
Sailingfool- Polysulfide-based sealants are probably the best choice for using with teak. The teak should probably still be wiped down with some sort of solvent prior to applying or bedding it in the polysulfide sealant, to reduce/minimize the surface oil at the time of installation.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.