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Italy 15-night itinerary & train travel

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Solo traveler, first time to Italy. Please advise on the easiest/least hassle routing:

11/1/2015: Arrive Venice ~8 am
11/1/15 to 11/4 - 3 nights in Venice
11/4: Take train from Venezia S. Lucia to Monterosso via Milano (1 change of train).
11/4 - 11/6: Monterosso
11/6: Train from Monterosso to Florence via Pisa (1 change of train)
11/6 - 11/10: Florence, take a day trip to Sienna
11/10: Train from Florence to Rome
11/10 - 11/16 Rome
11/16: Rome to USA

1. Train questions:
a. Is there any way to find out what direction your seat faces?

b. From Venice to Milan is a fast train and from Milan to Monterosso is an Intercity train, can get seat assignment on both.
I heard that Milan train station is huge and beautiful, will 40 minutes be enough to find my way to the Intercity train to Monterosso?

c. From Monterosso to Florence via Pisa:
Monterosso to Pisa is Intercity train, Pisa to Florence is Regional train. Should I buy the tickets even though there is no seat assignment for the Regional train? I read that I won't need to validate the ticket for the Regional train since the PNR code printed on the confirmation will suffice.
How easy is it to change train in Pisa?

2. I am concerned about hauling an 22" luggage and a carry on bag on the regional trains. It's a direct fast train from Venice to Florence. Will it be better if I leave from Venice to Florence on 11/4, then take an early train to Cinque Terre for a long day trip?

Thanks for your help!

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