He may be close, but he sounds kind of angry. Plus, I'd rather go for a short sail beforehand than have coffee or beer. It's cheaper, and I've found a lot of people (e.g., ones who've only taken ASA courses) can't steer worth a darn. And the crew should want to check the boat for holes and see what kind of a sailor I am. Perhaps I can't steer worth a darn, either.
I'm not sure why I'd pay someone to go sailing with them - any more than I'd pay someone to go on a hiking or bicycle trip together. If I find crew that can't do the whole trip, then one leg is fine. The only problem with doing that on the Chesapeake is that, especially once you cross the mouth of the Potomac, the distances by car to get back home for most people increase by 100 miles. One alternative would be to put crew ashore with an axe, some matches, and package of fig bars, but they probably wouldn't be there to pick up on the way back.