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Car rental/transportation for convoluted Tuscany-Rome-Tuscany-Rome trip

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Hello, we are trying to figure out transportation/car rental pick-up/drop-off that makes sense for our trip to Tuscany/Umbria/Rome. Our itinerary is a little messy, but dictated by family obligations:
Three of us are flying into Rome-FCO heading straight to East Tuscany (staying in Castiglione Fiorentino) for 4 nights, then to Florence for 2 nights.
Then we head into Rome for 2 nights to pick-up a family member (and say a quick hello to yet another).
Then four of us head to West Tuscany for 3 nights (staying in Volterra, we think).
Then back to Rome for our last 3 nights (meeting other friends).

We plan to have a car during each of the Tuscany excursions. Our question(s):
--Should we pick up the car initially at FCO, then return it at Florence-taking the train to Rome, then getting a second car for the 2nd part of the trip? And if so, where should we get the 2nd car?
--OR should we get the car at FCO and keep it until we get to Rome the second time? In which case where should we park the car in Florence and where should we park it outside of Rome to avoid driving in Rome the first time we go there (middle of trip)?
--OR--should we pick up our cars in Tuscany after taking trains to our destinations?
--OR--?? Other suggestions welcome; we've been combing through sites and can't figure out the best option for this convoluted trip.
One of us has been to Italy, but only to major cities on a guided trip with pre-arranged transportation.
Thanks for your help!

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