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wofat said:
...I am sure it will still be 2 to 3 PM by the time we're able to roll out the next day after getting checked out.

I can't imagine why. I think the latest we have ever gotten off, when we have chartered with Sunsail, was about noon. Usually more like 10-11am.

The "night before" thing allows you--assuming you get their early enough--to get checked out on the boat systems that afternoon/evening, and also to finish up your provisioning that evening. That way, the next morning, all you have to do is attend the mandatory chart review, and then head out.