Rome, Florence and Naples are well served by train. Use the Trenitalia website to check timetables in Italy. The timetable for the period from 12 June has not been published yet but you can use dates before that to get an idea.

Hotel bookings are not included. I often use Trivago.

There is no phone support but there is a contact form. For simple questions though this forum may be quicker.

EUrail is just the name of a pass-system, in force since well over 50 yrs. It includes most state-national railway systems anywhere in EUR. It assumes that people know how to travel by train as basics, and it certainly is NO travel agent.

For more general, tipical US-newbee Questions, use a general touristy site aimed at those, like tripadvisor. And-as always, google can answer an awful lot of 13 in the dozen general questions in a whim.

@James Chetwynd 
If you want to speek with a live agent you have to contact a travelagency.

Some travelagencies are specialied for Eurail/Railholidays and even offer “Packages” of the Ticket the Eurailpass (This forum here is to share experience or get an answer on problems related to the Pass), and Hotels. For example Eurailing Packages LTD. these are even advertised on the Websites of Eurail itself. But there are many many more.
Just few major examples (this list is quite huge)
ACP Rail
RailEurope (subsidary of French Rail)
RailCanterburry
FeestiniogTravel

Some like Euroventure (UK Based) offer even group tours means you can travel with foreign travelers together (With a “European Rail Tourguide” or without)

My experience is these Packages and Tour´s are often overpriced (ofcourse the travelagencies wanna earn too. and the Tourguide aswell )

If you have general questions about the pass we will try to answer it here But if you wanna have a full service experience with a live person i recomnend to use the service of a travelagnency :)