[Tidahapah]

Don't worry too much about the caulking.
As long as you have applied a decent primer and antifoul it should hold up for at least a few weeks.
I know when I built my boat we caulked her about 2 months before launch.
She still opened up a fair bit but with a big electric bilge pump (240 V0 not a small Rule or Johnston) she took up within 36 hours.
Initially the water rushing in sounded like a flood but we maintained the level low and just keept a watch for the first day or so.
Your local boys will have a good idea what is best and good luck.
By the way I like your traditional look, way to go.

Benn