Every situation is different. #1 communicate with the crew your desires. This is what we used to do when we ran crewed trips.
1. Meals, generally ate with the guests aboard as it was a great time to recap the day and get insight into what they wanted to do tomorrow.
2. Meals ashore. Sometimes we were invited and sometimes not.
3. Usually if the guests were just hanging out late. I would make sure the boat was secure and give final directions of anything that needed to be done, then I would go below and read.
4. Dinghy, if the guests were competent they could take it, but sometimes it is a lot easier to drop off and leave them with a radio, so no worries about losing the dinghy. Plus if we wanted to be social with friends we were not trapped aboard.
I will add, be specific about smoking or non smoking crew, it that is an issue. We would only do non smoking.

I think you will find it very relaxing to be with a crew and a good crew will let you run the boat with some coaching. A crew will know when to stop at certain places to avoid crowds plus no headaches with moorings or anchoring.