I don't think cruisers would require more logistical support, probably less.
In my vision it would work a lot like the guys that are getting up a group to cross the Stream. One says let's do it, others say me too!
I plan on sailing back down for 2 weeks in April. My wife can't get the time off so she's facing a weekend drive alone. Something neither of us is happy about. If there are other guys in my position, maybe the girls could share resources?
By the way, I don't mind if it turns into a race, I just don't want racing to be my only reason for sailing. Besides, I've always been a middle of th fleet racer so my finish is pretty well a foregone conclusion.