You will certainly want an extended visit before taking the plunge.
Visit. If you will be applying for an Elective Residency visa, you will need a registered lease in hand, and this would be the time to arrange one. Most of us living in Ascoli have used the services of a particular real estate agent, Cinzia Ventili (firstname.lastname@example.org), to help find housing. She is is strongly recommended if you’re heading to the Piceno.
Temporary housing. Quite a few AirBnB rentals are available in Ascoli. A local suite hotel (Di Sabatini) is convenient for stays of moderate length. Some folks have managed month-long stays through our local realtor.
Length of stay. Remember, you can only stay for 90 days on a tourist visa.
Small but important
Once you’ve made the decision to move, there will be a ton of things to think about. The big stuff you will probably already know. Here’s a list of small stuff that might wind up making your life easier.
Mailing address. You probably will want to keep an address in the US. This can be a friend or relative, or it can be a mail forwarding house such as USGlobalMail.com. With a forwarding house, you get images of arriving mail envelopes. You can ask for a scan of incoming mail (for a fee) or a shipment (for a larger fee).
Cell phone parking. You may want to keep a (cell) phone number in the US. There are multiple ways to do this, but the easiest way is to “park” your cell number with a cell phone parking service. Such a service can forward calls to you, or texts to your email. This is quite important for 2nd factor authentication on financial accounts, although not all providers will send challenge texts to “parked” cell phones.
International calls. You may want to establish a live digital phone number in the US, such as a Google Voice number. Having such a number will allow you to make free VOIP calls to US numbers. (Or you can make such calls with Skype for a small fee.)
Government benefits signup. If your plans allow you to enroll in Social Security and Medicare benefits before you leave, it’s much easier to do so from the US than from here.
Medicare Part B. Although you may choose to forgo Medicare altogether, if you are living outside the US when you enroll in Medicare, you are not eligible for the 6-month MediGap underwriting-free enrollment period. Keep in mind that Medicare does not provide any benefits outside the US (but some folks choose to keep it to avoid later penalties should they move back to the US).
MySocialSecurity and friends. You might be advised to sign up for the (free) online accounts offered by Social Security, the IRS and by state taxing authorities. These online tools allow you to monitor these bureaucracies without the telephone. You can sign up for these accounts more easily from the US.
US Amazon Prime. If you are an Amazon Prime video customer, consider keeping the service. The US version of Amazon Prime has lots of offerings that are not available in Italy.
When considering a move to Italy, the elephant in the room is often the question of taxes. Italian taxes are quite high. Some folks attempt to split the baby by residing in Italy less than 180 days per year (thus avoiding Italian taxes). This means that you won’t be a permanent resident, and thus won’t qualify for Italian State health care. So it’s a tradeoff.
If you do decide to become an Italian tax resident, remember these things:
Currency transactions. Financial transactions of all forms need to consider currency conversion. This is both complex and adds risk because traditionally stable investments such as bonds or CDs now have a currently fluctuation component for tax purposes (a CD maturing might give a capital gain in Euros but not in dollars, for example).
Roth IRAs and tax-free investments. Roth IRAs don’t exist here, so interest/dividend on Roth IRA accounts might be taxable. Similarly, tax-free investments in the US are not tax-free here.
Special treatments. Certainly types of securities (for example US Treasury securities) are subject to favorable tax rates in Italy (12.5%).
Sticky states. If you are changing tax residence from a high-tax state such as California, you may not want to use a California forwarding address. There is considerable evidence that California tends to adhere to previous residents longer than other states. So, it makes sense to avoid tempting the FTB into claiming that you are still a resident. For this reason, and among other things, it may make sense to change your tax address to Italy.