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Hi,
For houses in Asti you could check at casa.it or immobiliare.it (also available in English if you're not comfortable with Italian yet) but I'd rather use it to have an idea about costs than effective buying.
Scams are everywhere, and I suggest you to check in person all the offers. Since you have a bf in Asti and his family lives there, you should ask them for some help.

I can't tell you exactly about cost of living in Asti, but in northern Italy I'd consider around €350-€500/month for apt rental, depending on size, and position: cities are obviously more expensive than towns, and houses in the town center are more expensive than those in suburbs. Energy bills should be around €100-€120/month, but that really varies by house energy class and heating type.
Regarding food shopping it really depends on you: I'm single, living in the northern east part of Italy, and I spend around €120-€150/mo for food, but I cook everything on my own, and seldom rely on convenience food.

For the work part, that's a completely another story. There are no conventions between Italy and US as far as I know, this means you'll need a working visa to legally work here. Getting a working visa is probably as difficult as in the US: you'll need sponsorship, and the sponsor must prove there are no local workers available for your position. Bureaucracy might make it even harder, but that's just an educated guess based on my experience with residence for my former GF, which was a real pain no matter she was already EU citizen from another EU country.

I'm sorry that's all I have to offer, I really hope someone near Asti could help you more than me.
Wish you good luck! If you have any question, let us know.

Thank you so much for getting back to me. Are you American? Was your girlfriend American? Did she find work? I would be applying for residency visa. I have enough financial means for me to survive for quite a bit without working...although I do wish to work. I have quite a bit in savings and 50k in my 401k.

My only concern is work. I would hate to move there and then be unable to find work. Id even work at a restaurant or bar if it was available.

This will be a long post.

None of us are/were American, although I'd personally love to. I am Italian and my GF was from another EU country coming here as student, yet we had problem with residency (EU citizens are under preferential regulations regarding residency, especially for students).
Unfortunately, as i told you, bureaucracy here is the real enemy. If Asti's Town Hall is used to deal with foreigners, they will have good experience and help you. Since I live in a small town, and nobody from the office was used to deal with foreign students matter, we went through a real odyssey of nonsense, wrong papers and misguidance.

For your plan you'll probably need to ask for "permesso di soggiorno" for long periods, you can get it here locally from Questura within the first 8 days from your entry, but I strongly suggest you to call the IT Consulate General in SF (definitely convenient for you) for help. They'll know what to do for sure: since you want to stay with your BF for more than 90 days, I'm not sure you're eligible for Tourist Visa. Tell them everything, and they will surely help you.
Meanwhile, you can have a look at this site for all visa types and clear your mind a little bit:

Once you'll start looking for work, things will be getting harder though. If you want to work legally, you'll be required to have a work visa, and everything I wrote you earlier becomes true. Again, the IT consulate general in SF is probably your best bet to know what to do and how.
Honestly, I wouldn't see working in restaurant or bar as a viable option at all. Working visas are expensive and are usually for skilled workers: think about it, it's like I tried to get an H-1B visa to work at pizza hut. Even if I were able to find someone so dumb to spend thousands dollars for sponsoring me as a clerk, the USCIS would probably reject my application without even looking. (forgive any consecutio temporum mistakes here )
Italians aren't that different from Americans, after all.

Please don't consider me rude, and believe me I'm not trying to dissuade you to come here. I just think you would have better options with searching for a skilled job, but I'm probably not too comfortable with the language to sound polite. If you feel I've been rude, I do beg your pardon in advance, it wasn't my intention. If your first concern is work (and it should, I wouldn't use your 401k savings at all, really. That's your retirement, you'll need them one day), you should start looking for it right now: practice your Italian, use your BF and contacts in Asti for networking, send resumes online (ah, in Italy that's called Curriculum Vitae because we have a way with Latin, and we like it "long winded" but not so much. Google Europass CV for samples).
If you'll find work, it's very likely it'll be a little bit out from Asti, you'll need a car, and to convert your driving license, but that's life, as old Frank said. That would be a start anyways. Once you'll have your work visa, everything will change, taxes included.

I really wish you the best!
If you want to share your experience at the consulate general, I'm really curious to know it.

Ha-ha you were not rude at all! Thank you so much. I really appreciate your response. I would not touch the 401k but it would be there to show my assets. The first thing is to definitely learn Italian. I currently have a monthly income that I will be receiving for the next few years ($1250 per month) Although immediate work is not necessary it is something I would like to do. English teachers I have heard are also of great use. Asti is close to Turin or Alessandra. Perhaps that is a path I should explore.

Again you were not rude at all. I really appreciate your response. You are very kind. You are the only person from Italy that has reached out to me. It's nice to speak to someone who lives there and speaks English. How far are you from Asti? Perhaps we should keep in touch. My name is Darcy. Very pleased to meet you.

You're very welcome!
I'm so relieved you haven't found me rude!

Yup, being an English teacher is a great idea, and I'd suggest the business teaching path rather than the school one. Here managers and businessmen are getting required to know English or learn it, you could really get something out of it, and they're less annoying than kids, believe me!

With your monthly income you should have plenty space for having a lower wage at the beginning to be competitive, and grow in the future, that's definitely a path to try. I'd give a look to the Wall Street English Institute (wallstreet.it), and start from there. Nobody knows.

About me, I'm near Padua, around 20miles far from Venice. Not that close to Asti, but surely we can keep in touch, I'd love that. Morover, I'm curious about your experience with the consulate, remember?
Oh, I'm Alberto, by the way.

Hope to hear good news from you soon!

Hi can u share ur Whatsapp we can conversation about topic my no on whatapp **

We can talk here.

Hi Darcy.
I am John. The advice you have received from Alberto is sound and yes Wall Street is a respectable English teaching school to professionals and people. Not a classroom of 35 children but more a room of max 5 "ish" people.
I am from New Zealand and have lived here in Italy for nearly 6 years and although I have had it easier than most due to my Rugby sporting back ground and level played at i have found it not that easy.
In my line of work (professional rugby coach) the money here in Italy is extremely low. In Japan in 2002 I had a contract of a $million. Here we are lucky to get €20k.
Wall Street pay from €15-25 an hour depending on your experience.
If you were moving to Bergamo I could put you in contact with a school there which is very good.
I coach close to Bergamo in a small town called Dalmine.
I live in milan.
I wish you all the best and if you feel like staying in touch then please do.
John

John

Thank you so much for your reply. I'm in Asti right now. But moving here seems like a distant dream. My partner does not want to remain in Europe. He wants to move to America. I wish to remain here. Cost of living here is so much cheaper in America. I try to explain this to him...but he is uninterested. It's sad. I desperately want a diffrent life.

I would love to keep in touch. My email is darcylewis79@gmail.com please email me anytime. Also you can reach me on my Facebook. Darcy doni.  I look forward to hearing from you again John

***Cost of living here is cheaper than america

😊😊

Hi Darcy:

I would have to agree with Alberto...securing meaningful work in Italy as a foreigner is quite difficult.  My husband (who is Italian) often says "Italy is the perfect place to live if you don't have to work." 

I ended up working as an English teacher but it paid quite poorly and in the end I didn't enjoy it at all.  My advice would be to find work that you can do remotely (some type of project work in your field) with a US based company or as a freelancer.  Ultimately that is what I did and now we go back and forth between the US and Italy.

You are right-the cost of living in Italy is much lower than the US (not to mention an arguably better quality of life), but you should not use all your income to stay here.  And sadly, if you BF is longing for a different life in the US as much as you are longing for one in Italy, this will likely be a problem going forward. You may need to make your decision independently of that-you also may find that in the longer term, you won't like it as much as you imagined and you want to make sure that you keep your options open for going back to the US.

Best of luck to you!