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Italy trains and car hire

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We will be in Italy for 15 days end of June into early July.

How far in advance should we make any train reservations we may need. We are trying to decide on car rental which will help decide on the train rides we may need.

Venice is our first stop then going to friuili for two nights, on to Bologna for three nights before going to Tuscany for one week.

Should we rent a car for the drive and two days in Friuili drop off the car, train to Bologna, then pick up a car again when heading to Tuscany or keep the car the entire time?

Looking at Auto Europe website it gives me an option with insurance and an option with insurance without any deductible. What does everyone normally choose? In the US we normally do not take insurance as it is covered by our regular auto insurance and also through our credit card. Not sure if insurance in Italy is automatic without option out of it.

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