My parents just retired in Italy this year from Australia. I have been in Italy for 2 years and prices here are much lower than in Australia so they thought they would save a lot of money. I can tell you what I remember of their experience and hopefully it is accurate recollection.
The main thing they found stressful was not knowing the language. Don't expect many people to speak english here as you'd be lucky if 2 in 10 people understood a word of english (which surprisingly we found the French to be very fluent in English and able/willing to help. My parents stayed in France for the first 6 months. But most of the Italians are friendly. I am not saying Italians should know english only warning you.
My parents found that the realestate agents were very laid back and casual and they had to chase them up when interested in buying a property. In Australia the real estate agent would be calling you 30 minutes after the inspection to close a deal. The positive is there is less pressure.
The real estate was very helpful in assisting them with the financial, bureaucracy requirements and residency issues. The agent took them straight away to the bank to open a bank account and to the council to get a "permesso di soggiorno" (it's something you get before residency). They had to go the local polizia in the area and my mother was a British citizen but my father was Australian so he wasn't in the EU. They seemed very worried when they saw his passport and waved their finger at him "you can only stay 3 months, you must go back to Australia and to the Italian consulate to get a visa" which they were doing anyway (luckily there was one policewoman that spoke a little english).
If you buy a property you can get residency but there was a problem when signing the documents that only my mother could take ownership of the property because my father wasn't a resident yet which was ok but they would have preferred it the other way. So my father was the only one with residency issues because he wasn't in the EU.
They returned to Australia for a month and everything went smoothly. There were a couple of scares such as booking an appointment at the consulate which ONLY could be done online and there was only one available appointment appearing so do it as soon as possible, especially when you only have a window of 1 month. Then they found out at the appointment that it would take 2 - 3 weeks to process the application which was exactly the time they had in Australia and cutting it fine. Luckily the consulate official rushed it through and had it ready in 4 days.
Returning to Italy my father then had to go to the council then to the health department and fill out a form. He had to declare their salary from last year and was charged a percentage of that for both his and my mothers health cover (I think that is a one off payment). You need health cover before residency. Then he returned to the council and after a week he had his official residency documents. There was an ID card that they had to organise afterward which is needed, I don't know why they don't give it to you with the residency. In this respect my parents were very lucky to have 2 women at the council that were extremely helpful and friendly, one of which spoke a little english.
They are now awaiting a police officer which randomly comes to your premises to ensure that you actually live there. My parents found the property in a British real estate magazine for Italian properties so if you don't know the language it is very helpful, especially when getting advice on closing a deal.
A couple more observations are that you can't pay cash for anything over 999 in shops which I found crazy (usually you get discounts for paying cash). It has something to do with stopping tax evasion. You also need residency to buy a car in Italy. Italy has a license/tax if you have a TV. You will need to resit the tests for your drivers license again (written and practical exams, even though Australia allows Italians to exchange their license over), and you can't do them in english only Italian, German or French!! You can use your US drivers license for one year after you get residency (with the International drivers permit).
WARNING: You must be careful when buying a house in Italy that the regulations are correct. On several occasions the height of the bedrooms didn't fit regulations as being able to be inhabited (you officially were not allowed to sleep there). There is also a regulation on the amount of light entering the room which you find insufficient in some places. It usually happens in ground floor/basement apartments which are usually the last ones to sell, probably because of this problem. They found several quality and regulation issues with the places they looked at so be very careful. The real estate agents simply shrugged their shoulders and said "it's no problem, it's what happens in Italy" but at the end of the day it will be on your head. One thing I was surprised at was the lack of craftmanship in Italy, I thought it would be much better.
I'm sure there is alot more but it's all I can remember for now, good luck.
PS Let me know if you want to know something specific and I can ask my folks.
EDIT: Just remembered, my parents applied for a debit card so they can withdraw there own money from their bank account from ATMs and the bank called and said the government is investigating them but not to worry!!! The manager of the bank called them in and was very embarrassed and said it was the way things worked in Italy.
Italy has a massive beauracracy and works very inefficiently sometimes (ie they increase taxes and introduce new taxes to get more money instead of enforcing tax laws and catching the many that don't pay tax here. There is little point in rising taxes when no one's paying them as you will only hurt the honest ones that are forced to pay for the bad. Effectively they are rewarding tax evaders and simply place silly laws to attempt to thwat them (like putting a band aid on shot gun wound).
Traveling to Italy
Getting married in Italy
Childcare in Italy
The Milan neighbourhood guide
Buying property in Rome
Connecting to the internet and using phones in Italy
Pregnancy and childbirth in Italy
Buying property in Milan
