re: 24 Hours in each of Milan, Venice, Florence, Rome; what are the absolute must-dos of each?

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absolute must-dos

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Skip Milan unless you’re flying to/from MXP
Then just take a fast train to Florence or Venice or Rome

Now that you’ve limited your number of stops, what’s most important to you? Art, history, food, live performance, natural beauty, local culture? Meeting people? What’s most meaningful to you? That answer would narrow down what are the must dos.

I'd still either skip Milan or spend one day there. Add in something like Cinque Terre, Bologna day trip, a small town in Tuscany.

2-3 days in Venice, 3 days in Florence, 2 days in Cinque or Tuscany, 3 days in Rome

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- Duomo, including the roof

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I cannot comment on the roof because we did not do that. But the inside of the Duomo is nothing to wait in line to see. Bland. The outside is spectacular.

#1 on your list should be Michelangelo's David. It's truly impressive.

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Would you skip one to do 48 hours in another?

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Most will say its a horrible idea but if its most likely the only chance you will ever get it is as good an idea as they get. That said find a tour that handles EVERYTHING. They will rush you in and out but you will not have as much likelihood of missing trains and busses and flights and having problems at hotels and restaurants....to do what you are planning takes some tight scheduling that will get tossed to the way side with one mis read sign in train station while panicked to get to the next location. There are a BUNCH of people who do Europe like this....obviously it isn't immersing yourself in Tuscany for 90 days straight but if its unlikely that is ever in the cards what you are describing is better than nothing and, with the right mindset, it could actually be fun and an adventure.