Thanks for your great advice and kind words. We've been away all week on the boat so I am just back to this thread now.
I do think it would be a bit much for a delivery captain to be on a 38' boat with all of us. I don't think I would feel too comfortable being in tight quarters with someone I don't know either.
Taking an offshore/blue water course would be ideal. I am really leaning towards putting this off until next year and spending next summer sailing all around maine and gaining more experience. I believe there are offshore sailing courses offered up here so I'll have to look into that.