Reg,
Good to hear you can join us and, yes, that is now 2 BRes including mine.
If we sail out of the Sail Academy, which is my plan, then there's loads of space for cars and trailers and they can remain hitched. Launching from there is more expensive than the Weymouth slip but parking and logistics is much easier.
If you are sleeping on the boat then I recommend putting it in Portland Marina, which is adjacent to the Academy. The cost is £18/night but the facilities are excellent. If you want to slum it then you can probably sleep in the boat on its trailer. If that's your plan then I'll check with the Academy whether they are OK with this.
There are plenty of B&Bs in the area. The ones most local to the Academy look more "functional" or you can drive 5-10 mins further and be in the proper Weymouth "seaside" B&Bs. I am investigating options (although probably won't have anything to report until after Sail Caledonia).