This post from the best-of-class Girl in Florence blog — despite its title, “Why Moving to Florence Might Not Be the Best Idea for You” — could be taken as a guide to why it might be the best idea for you and help you make the most of the pros and handle the cons (in both senses of the word!). Georgette, code name: Girl in Florence, offers a spot-on list of the good and the bad. Some points, of course, are subjective, relative to your previous life experience, such as “Con: Weather isn’t always warm and sunny, we can have long hard winters and plenty of rain.” I’m from Oregon and lived in New York for years. I can tell you about rain and hard winters and Florence ain’t got ’em. Or “Pro: free health care” might not seem so special to those of you not from the States or other countries without that blessing.
Pros
“You can meet some really incredible people here, Florence tends to attract a varied population.” “Impressive expat community, everything from drawing clubs to mom networks.” “Aperitivo is a religion here, embrace it.” You can tap into this community and varied population at Speakeasy Multilingual Happy Hours and other groups or by joining group activities or volunteering. “Free health care” if you’re in the Italian health system. If you’re a student, retired, an au pair, etc., you can pay an annual fee to join the system. If you’re not in the health system or want private care, it is also reasonably priced. These are some doctors and dentists we suggest.
“Great day-to-day lifestyle, people walk/bike everywhere.” As far as I’m concerned, biking or walking are the only reasonable ways to get around Florence.
“Affordable organic fruit and vegetable in season.” Befriend your local produce seller or head to San Ambrosio or Mercato Centrale.
Cons
“Rent can be high and pickings can be dismal as more apartments are turned into Airbnb investments.” Like the weather, this is relative compared to where you come from, but the average-salary-to-average-rent ratio is rough. We offer tips here and can hook you up to our partner agencies and landlords. “Bureaucracy is annoying, red-tape is a daily reality when it comes to everything from signing up to a local university to renewing your visa.” I would vote this the most annoying thing about Italy in general, maybe because in my neck of the woods, Oregon, bureaucracy tends to run more smoothly. We can hook you up to a professional who will help you through it. It also helps to learn the phrase, “Che palle!” [What a pain in the ass!] and say it often with attendant gestures. “The average salary wavers around €1,000-1,200 a month.” “Lack of jobs, many people work on short term contracts (if they are lucky) or have a partita iva (freelance) which is costly.” Technically, the average salary in Italy is €2,000 a month, but surely the wealthier North is pulling that number up. This can be a dealbreaker if you come from somewhere with a better economy and higher-paying jobs. We give some tips here on finding a job in Florence. It can also be a great place to be a “digital nomad.” Freelancing isn’t always costly for taxes. Find a good accountant to know about out what taxes you would pay. U.S. citizens generally are required to pay social security and, therefore, not Italian social security, known as INPS, which makes a big difference. If you’re not making money and paying taxes in Italy, rather than open a bank account here, just get a Wise account and bank card to move money from non-Italian accounts. 
For expats, international students, and anyone who needs to send money between currencies and countries, Wise is far and away the best option. Use this link to get your first transfer free.
“Making friends can be harder than it looks, locals are a hard nut to crack (not impossible) and people come and go quite frequently in Florence.” This is the downside of the international community. Not everyone stays long term, especially if they haven’t cracked the also hard nut of finding decent employment. Still, at Speakeasy Multilingual, about half of those who come, Italian and otherwise, live here permanently. “English is widely spoken which means you might not feel forced to speak Italian.” Definitely take Italian lessons and insist on speaking Italian as much as practical and polite.
More plus sides:
The weather is mostly nice — from the perspective of an Oregonian — except for too-hot summers and a couple chilly months in the winter. It’s a good starting point for trips everywhere in Italy and much of Europe. It’s not too big or too small — from the perspective of a small-town girl who moved to New York before settling in Florence — 350,000 people and you can bike most central places within 15 minutes. Art. ‘Nuff said.
Food. Gelato. Pizza. Wine. Spritzes. Prosciutto. Tomatoes. Olive oil. Mozzarella. Schiacciata. Olives. Steak. Salami. Bread (but not saltless Tuscan) bread. Cheesecake. Lemons. Pasta. Pasta. Pasta. Pesto. Ragù. Coccoli. Stracchino….Did I mention food?
More downsides:
Mosquitoes. So many mosquitoes. Invest in anti-mosquito devices. Air pollution. It’s not quite New Delhi, but it’s a problem because of the bowl-shaped geography of the city and narrow, smog-trapping streets. Less smog has been one of the silver linings of the 2020 lockdown. Too many tourists. 2020 has taught us that tourists are a mixed blessing. The huge thinning out of their numbers is devastating to the economy and the livelihoods of so many people here. But it makes it easier to stroll pleasantly through the touristy areas without feeling engulfed. Anything to add or subtract? Put it in the comments.