Here are the options I have found (leaning towards the first):
Very Nice, 10 min walk from duomo
Decent, great location
Originally I was thinking that Milan did not have as many sites I wanted to see as other cities, but the more I research it, the more historic beautiful sites I find. The blogger "sushi75" from the Lonely Planet website is a Milan expert and took the time to recommend some fabulous walks from the Duomo here. I am definitely going to be doing some of these walks!
Hopefully Anthony will have been able to sleep on the plane and we can have a full day of exploring Milan the Saturday he gets in. As of now, we are planning to only stay one night in Milan, get up early, enjoy un cafe and a morning stroll in Milan, then taking the train, head onward!

Our general plan as of now is as follows:
Milan --> Verona/Venice --> Bologna --> Genoa/Cinque Terre --> Florence --> Sardinia --> Rome
Quite a bit of traveling in our 2.5 week stay, so we may be forced to edit a city or two out in order to fully enjoy ourselves in each cite. Anthony and I have taken the night off of work tonight to set in stone our official plans and book our lodging. So those real plans are soon to follow.

