Okay, let's start looking at this from a practical viewpoint.
1. I agree that Lugano is nicer than Milan but I doubt I will be able to make the restaurant reservations there. Do we have anyone who can take that on?
Making the reservations in Milan would not be a problem.
2. If you are flying in, it makes no difference -- either way you will fly to MXP.
3. If you are driving from the North, Lugano will be about an hour less on the road.
4. Is the middle of the week okay? Otherwise the only Saturday between Christmas and New Year's will be Dec 30 and I think most of you will want to be home for Dec 31.