Having been a renter in Italy for 12 years I think you would benefit from working with an agency, because rental agreements are complex, come in different categories, and are very binding. However, few if any rental agencies will take you seriously unless you are on the ground, in Italy, searching in person.If you absolutely need fast internet to do your work then consider working with an agent to get a guarantee of internet service in the contract. Most landlords will tell you internet is no problem and fast -- but that might not be the case. For a variety of reasons, internet and wi-fi might be sub-optimal in a particular location. You should familiarize yourself with what other independent businesses do in your target areas, what providers they contract with. Despite having your own income you will still need to carry health insurance to qualify for legal residence in Italy and if you are in Italy for extended periods, it is highly likely you will be required to pay income taxes and meet other filing requirements and declarations regarding your assets and income, even those you might keep in the UK, subject to severe penalities if you do not comply. I don't say any of this to frighten you but only so you don't get a truly nasty surprise and jeopardize your future happiness in Italy! My experience of living in Italy is that I did all the adjusting to its culture. Italy did not change for me. I happen to like what Italy is and hope it does NOT follow the rest of Europe, the UK or the USA into prioritizing wealth over community and preservation of tradition. But that is for Italians to decide. Hope you find your sweet spot!
Lots of helpful advice above but I will say that going on 10 years plus in Italy, in a town with some but not a lot of English speakers, I have never gotten depressed, so it's not inevitable. I have had the usual run of bad experiences one can have anywhere over a ten-year period (things breaking, some plans not working out, health emergencies or sprained this or that, things where I needed a lawyer) but to the extent I compare my situation here with what I'd be experiencing in America, I think I've got plenty to be happy about. All that said, if one does get depressed, wherever one is, it's always good to remember it's not an unusual thing and nothing to blame oneself for. Who knows? I might get depressed tomorrow...Also regarding trains: There are many parts of Italy that are very well served by the train system while other parts are not, but in actually quite a lot of central and northern Italy, and coastal Italy, it is possible to live in a very small town or smallish city and have a short walk to a train station. And if one is more distant from the train station there is a frequent bus to the train and it is usually possible to develop a relationship with a taxi driver for those days when you need a ride to or from the station. I've lived without owning a car for 10+ years and not found it a problem at all. (Where I live it would be just as hard to find daily affordable parking for a car as it was when I lived in Brooklyn,and possibly worse!)For me, overall climate and food were some of the most important considerations for choosing a place to live. I like to wake up to sunshine as often as possible and I like to eat seafood and fresh fruit, so I looked along the coasts, where the train options are plentiful. But if you want to keep Florence in the mix, and don't care about seafood, you should check out some train routes that would eliminate the need for a car.
Since you mention "year round" do be aware that the northern lakes areas can get snow cover in winter, and plenty of days with low temperatures. Coming from Rotterdam you might not care, but if you do, then the mediterranean coast near Genoa or Savona only adds about an hour more of driving. I don't know if your budget is enough for that area (if you don't demand a seaview, I would think so). However, I suggest that you buy (or rent) a place where you have a caretaker or landlord right on the property or in the same building. I rent an apartment in Italy, and when I need to go away for weeks at a time my landlord makes sure everything is fine. He lives in the same building. Although I live in an apartment building, you can also find apartments for sale or for rent that are on farms or large pieces of property, where again there is someone around all the time who keeps an eye on your property. Italy is a very safe place with low crime but it also is just a fact that the holiday-apartment and holiday villa areas are well known, and everybody knows that many places are vacant for many weeks of the year. So you need to be a bit mindful of security if you are going to be an absentee owner or renter. There are many beautiful furnished holiday apartments where the landords would be thrilled to have just one renter paying rent year round. So you can often negotiate a nice deal, and the landlord will take care of the property when you are not there.
Chiusi is a lovely, untouristy place but close enough to major English-speaker tourist draws like Cortona and Montepulciano that an English-speaker not yet fluent in Italian might easily find companions and activities to bridge the gap while making a transition.
That look enchanting!
One suggestion I would have if you are looking to buy an apartment, get a top floor. You don't want anybody above you. Excellent advice! Especialy you don't want an overhead neighbor who wears high heels.
I would say broadly speaking that very small towns are cheaper than larger towns and cities, and water views are expensive no matter which water you are looking at. If you can avoid owning a car, it will greatly reduce your living expenses.
Oh yes, certainly possible to escape American culture in Italy! And in the part of Liguria where you are looking you will rarely encounter Americans. I wasn't understanding what you meant about mentalities and Rhode Island, etc. All that said, young Italians do want to experience some of the trendy and untraditional things that are popular in America. Avocodos and craft beer were nowhere to be found when I moved to Italy, and now my tiny fruttivendola stocks them. But if you stay out of the places most popular with American tourists, you will not only have escaped America but quite a big chunk of today's homogenized global corporate culture.
I think if finding English-speakers is a priorty you are going to have a hard time beating Lucca unless you go to Florence. Prato is significantly dominated by Chinese immigrants and Pistoia is, to me, an enchantingly typical small Tuscan city, but it I think it is thoroughly Italian. One smaller Tuscan town that is a bit more "international" is the arts colony of Pietrasanta because it attracts an international co-hort of sculptors and sculptor-students. If you are priced out of Lucca you might want to check it out, but it is not convenient to your plans to visit Rome a lot. Cortona might work for you, likewise Perugia -- but I don't think these places are cheap. But another town with a fairly long history of English-speaking colonization is Gaeta, on the seaside south of Rome, partly because of the American naval presence there and also a little bit because the American artist Cy Twombly made a home there. There is public transportation from Rome and you would not need a car living there. Where is your own family from?
How much space do you need and how much time do you plan to spend each year in Italy? If you look at all the financial implications of living full-time in Italy -- taxes, health insurance costs post-Brexit, you might find it financially attractive to rent for some months of the year rather than buy. Especially in the area you are looking at, rents for attractive furnished apartments can be low. Many landlords offering holiday apartments would be thrilled to have a tenant from, say, October-Feb only, and might give you a nice deal (so long as you pay for utilities). As for the "italian mentality", not sure how that gets identified in Rhode Island (never having lived there), but there is really almost no place in Italy where you can go anymore where you would find the kind of expat colonies of English-speakers one finds in Spain or Portugal or perhaps parts of France, where local Italian culture is co-equal or is dominated by English-speakers. It would be easier to find if you were Russian, acutally! Or Chinese or perhaps from Africa. Once upon a time quite a few towns all along Liguria had significant enclaves of British expats, well established, and there were lots of amenities for them: All-English libraries, pharmacies, churches, cemeteries, tennis and golf clubs -- the whole pot of tea. But after the devastating World wars, the British never returned in large numbers, and were supplanted by different holiday makers, mostly Italian. Americans rarely even go as tourists to the parts of Liguria closest to France. Sicilian culture in my experience is less integrated into overall Italian national culture -- there is a firm sense of Sicilian identity "first" that reminds me of talking to Texans --so it is a bit more exotic -- although I find Palermo to be a very cosmopolitan and sophisticated place.