Friday or Saturday would be it for me. Getting up at 5:45 during the week doesn't make me want to drink and stay up too late. How big is the room for this? Just hang out in the back of the shop while open, or after hours?
Here's a thought. Have "selections" for each event. From mild to full flavor and such. Different choice each time to broaden each smoker's horizon. Wouldn't be hard to get the smokes together seeing as how it's at a shop. Possibly have a scotch of the evening, maybe two. Everyone who wants some of it would buy in before the event, maybe through paypal. That way it wouldn't be a hassle once we were there. I really like this idea.
Of course, Bob could provide some "specialty" cigars as well At a cost that is.