1: Most Nokia phones running Symbian would fit the bill, for example the E51 which I just bought or the 6120 classic. They cost around 200€ without a contract (which would make no sense for a few months). Note that in some countries, it may be difficult to get a card, even pay as you go, without a permanent address.

2: I can't answer the question about network charges. Remember that you have to change from carrier when you change from country. Only thing: data charges are a racket (maybe less so in Italy).