I'd say forget about the opponent and run stuff we plan to run. Probably give the young players some minutes more.
Real Madrid will be some good test. Very experienced team, half of the Spanish national team plays there + veterans such as Ayon and Nocioni. I haven't watched Milano in a lot of time.
I will care who wins just as much as I care who wins a Summer league game. The more important things to me would be lineups tried by Brad, how well we rotate defensively, what stuff do we run on offense, etc...
And no injuries!