how did it go, which Bay?
The mouth of the Chesapeake Bay, we haven't tried it yet. The couple went back to Pa. for a week but should be down soon for another month.
We are having our dog days of summer now which means not much wind and a good chance of severe afternoon thunder showers, not good for a Bay crossing attempt.
Hopefully we will get a chance to try out some configurations and test feasibility by attempting to sail a course close to shore and then maybe the Bay but we wouldn't have much in the way of equipment nor a chase boat.
It is about 40 mile round trip and is very doable on an Island in a day but not to sure it could be done hooked together. If so though it should open up a whole new world of possibilities.
On your seal I would recommend goop. I used silicone the first time and a vinyl repair glue the second both did a much neater job than the goop but nether lasted long. The goop is there to stay and I used plenty.
I also have a feeling that I am getting water under the mast fitting on the deck. I noticed it because of the hull getting water into it when it rains. The way it sits on my trailer the water will pool up against the rise in the front deck ahead of the mast cup.