Not sure about the illegality of the Europe sectors as it depends on the origin and the purchase of the visit Europe pass being a separate ticket which removes the issue.

As for that damn 2200 arrival at MXP, I get that a lot. The best hotel around the airport is the Villa Malpensa which is about 800 metres away. But the shuttle bus has stopped running so you need to phone as soon as you land, at your expense, and they may ask you to take a taxi for about 15 euro. Stuff that, I walk down the road. There are plenty of other hotels around the airport but they all cost the same when you add the taxi transport into the equation. My advice is
1. everything will be shut on arrival at MXP, change your money before you go as the always open Forex shop staff tend to disappear to some staff canteen
2. get to bed and get up early and take the train into town.
3. sometimes the train into town has stopped running at that time of night and a replacement bus service operates. Firstly you won't get on the first one as it is full of everybody before you so you have another half hour wasted and secondly the bus takes ages to get to central milan and then you have to get a taxi if you can find one and ..... Midnight at your hotel.

As for my preferences for a day, I would rather go to any of the Scandinavian capitals than the south of France and HEL is the best mileage run. Which FFP and which class of travel to advise further on the best mileage and status from LON.

As for not sampling the delights of LGW, I will take that personally! Your getting the beer at LHR for that one, even if BA are paying.

Happy landings and may the status points be with you.