PaulK, thanks for the advice. I am thinking along the same lines.
I will have four, maybe five, with two of the crew fully qualified to run the boat and two or three with less experience. I plan to have two on watchand bring a fresh crewman up every two hours. The "watch captains" alternate, as do the newbies. The first watch captain stands a short two hour watch, then everyone gets four on / four off for the 1.5 to 2 day run.
The only down side to this is that someone is rattling around down below every two hours, but on a 36 you pretty much hear everything that's going on anyway.
We plan on going offshore a bit for better breezes and perhaps flying an asymetric spinnaker. I'm thinking if a spinnaker gype is required, we could do it at the watch change when we have three people on deck.