How do you choose where to stay when travelling?

I'm planning my first proper solo trip next year. I'm headed to the F1 in Italy and have the choice between staying in Milan or Como.

Milan is more expensive but better connected. Como is cheaper, calmer and stunning, but harder to get to the airport for my flight home (which is at 10:35am, so I'd like to be at the airport by 8am).

How do I make this choice???