I don't want to rain on your parade, in fact I think this sounds awesome. But I really think you should stress personal safety. Each time I've done this sail (3-4 times) I've gone with a group of my buddies and each time at least some of them have been completely out of site even though we said we wanted to stay together. Some times it was due to fog/haze, sometimes it was because I was so damn fast I sailed away from them (OK maybe they sailed away from me...
). If this was a race I can't see how 2 chase boats can keep an eye on all of them.
Obviously it's your call but I would highly stress being prepared with at least VHF, GPS and flares. That way they could call the chase boat and ask for a ride. Or if it comes to it call the coasties and ask for a rescue.
Also have you thought about housing? If you wait until the peak season is over you can rent some of the employee housing for really cheap. It isn't luxurious but the price is right. We affectionately referred to it as our lawnmower shed! But it has been a couple years since we did this, things might have changed.
-Eric