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There is masses of information on the subject, perhaps far too much. You will find it here and on many other forums. Best way is to break it down to the subjects you come across, your own list is a good start. So if you start looking for a subject like "residency Italy" on forums or just as a web search. Apart from getting answers to your question you will come across many more subjects and then be able to build up a picture of each. There is an awful lot to what you are planning to do, but many have done it. A lot of the answers to your questions will depend on your circumstances e.g. not in receipt of a UK pension means you do need to look at the cost of health care.

see > http://www.prefettura.it/roma/contenuti/4944.htm

I should start by reiterating living in Italy brings lots of hassle, but we would not change a thing and doing so is worth any hassle we encounter…If you are in receipt of a UK retirement pension (state) you can ask for a form S1 to be covered on your UK national insurance. There is nothing to stop you going back to the UK when your retirement pension is payable and state you are living there, get your form and then go back to Italy with it. You would in any case always be covered in Italy for emergency treatment with or without this form or any other cover.That brings me on to the matter I raised in my earlier post, individual circumstances are paramount regards any answer you get. Bearing that in mind you need to consider what you can or can’t do if you do not have a UK address, or for that matter if you do retain one. Things like driving licence come to mind, bank accounts, insurance and jury service etc. I’m sure there are many more, but they are either small or not frequent enough for me to remember. Think about everything you do in the UK and then think what would I do for that if I was in Italy or living in both countries… At least you have lots of time to consider your plans and you should use it to your benefit. Whatever you do, don’t be rushed (by your own enthusiasm) into something you may regret and find costly. First step might be to rent in Italy for a short period. Just read a post recently on a local forum where someone wants to rent their place for 3-6 months over the winter. This could be a very cheap way to get a feel for living here. The place in question seemed a little too rural, but again that depends on your own personal preferences. We took 2 years to find our place here and that included 5-6 months renting while looking  at many, many a house…