I'd like to know how it works out differently from breakfast when we're trying to hustle them out the door and in the evening when it can be a relaxed, hour-long dining experience.
I think that's what I would focus on, relaxed & casual- it doesn't have to be a rush, they don't have to be anywhere (or do they?) and the time constraint is really how long you want this to take.
Let us know how you planned out that part- how long you were going to devote to serving dinner, cleaning up and prepping for tomorrow. Also want to know if you will stick with multiple menu offerings or have a set course after this experiment. Is it BYOB? Can the guests have their own wine or can you provide wine?.
Our breakfast experience is different than most...we deliver breakfast to their door in the morning...knock and run away! We don't even have a dining room.
So, when planning on serving dinner, I figured I would do it the same way. Well, it's a combo of both it seems. I prepared their soup in bowls and had the soup and silverware, napkins, etc. on a silver tray when I first knocked on their door. I actually went into their room, set the soup & things on their table and left, telling them that it would be another 10 minutes before their dinners were delivered. This gave them time to eat at their leisure.
Here's where the timing is critical (as it is with our breakfasts for delivery). Everything has to be ready and plated to deliver on the large tray we use for breakfast. By the time I delivered the main, they were done with their soup, so it was perfect timing.
I then took everything off their tray and placed it in front of them, which seemed the natural thing to do. It's weird for me, since we don't "serve" at breakfast. I came back with the soup bowls and empty trays, then quickly returned with their desserts, which I placed on the table outside their door (where we typically leave the breakfast tray). I figured they could get up and get their dessert when they were ready.
I then told them to place their dishes outside their door when they were done so they could take as long as they liked. I gave them some sheets of aluminum foil in case they wanted to save any leftovers. At this point, they were quite happy and excited and said how special it was to have their own personal chef...and commented that they wouldn't be able to go any place else to get this kind of service.
If I had to wait around and serve the different courses instead of deliver it, it would take a huge amount of time out of my night and I probably would get burnt out quickly. I know that most places are not really set up for their guests to eat in their rooms, so my method wouldn't would for them.