Ciao. I do not work for ItaliaRail. I am a fellow traveler like you. We are going to Italy in September. We are a group of 6 and I purchased all of our rail passes last weekend on line. We are traveling from Rome to Venice, Venice to Florence, Florence to Cinque Terre and back to Florence, and Florence to Rome.
I agree with Mike, the CEO, ItaliaPass team. When I looked at passes, the passes seemed more for longer travel and seeing other countries.
We have a friend who travels to Italy frequently, and he recommends purchasing the Business Silent tickets. This means no cell phone use allowed. He says Business class is more comfortable, and I did not find it too much more, all things considered.
I did make a double booking from Florence to Rome thinking that I was booking Florence to Cinque Terre. It seems that the rail to Cinque Terre is regional transportation. ItaliaRail has a toll free number in the United States and they have customer service reps available for most of the day on the weekends. I did not have to wait on hold too long, and the rep, Nicole, immediately refunded one of my double bookings and assisted me with finding the regional route we wanted.
I was very pleased with both the website and customer service, and I was able to print all of our documents at the time of booking.
I recommend not waiting too long to book as I found the return to Rome from Florence was booking quickly. Some of the route times we were interested in did not have available seating and Business Silent was not available and we paid extra to upgrade. Seeing as that is our second to last day of a 3 week trip, we felt it was worth the comfort.
If you are hesitant to book yourself, I highly recommend contacting customer service directly for assistance. It was some of the best customer service I have encountered in some time.