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Itinerary help: northern Italy with car (mostly)

I would like feedback/help on the following itinerary for our trip to Italy this fall. Our travel dates are Sept. 20 - October 5; our flights are booked.
The basic destinations are: Dolomites, Lake Como, Siena (with day trips), Florence (with day trips). I've indicated where we've been before, if applicable. Questions follow each section.

Day 1: Arrive Venice @ 11:20 am. *(We have been to Venice twice and are forgoing it this time. We arrive relatively early in the day, so will pick up our rental car right at the airport and head towards the Dolomites.).

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