I live in Italy for 8 months a year and the other 4 months I come back to the USA and work at a high season , high tourist resort job. Since the cost of living is so low in Italy, even with the exchange rate, it is possible to rent something for $600-$1000 a month furnished including utilities.
You can rent a fully furnished apartment or room with utilities and internet for less than taxes and insurance on my home in Florida…which I liquidated and rent out to cover the mortgage. Rent your home furnished if you can. You will get pennies for furniture and housewares anyway and it will save you a lot of hassle. Don’t pay to store furniture. It takes up a lot of space and you may never use it again. Choose your renters carefully or hire an agency. They usually take the first month for finding a tenant and 10% for collecting the rent. You will be surprised at who is renting these days.
Then, in the winter time, I return to the USA and work in a high season , high tourist job where I am tipped. This way, I am living where the temperature is the best, the town is hopping and I am sure to get a job and tourists are abound with money to spend. In winter, high tourist areas are Aspen, Key West or Palm Springs/Phx for example. If you want to live in the Carribean or Mexico, your off season would be summer, so your high season would be Alaska, Hilton Head, Nantucket, Cape Cod or expensive resort town.
Take any job where you are tipped, so wait tables, cocktail, bar tend, hotel nanny, valet or bell hop, concierge, or beer babe on the golf course. Choose your place based solely on how much money you can make in a short period of time, so you don’t have to work for the rest of the year.
Rent a room from a local in their home ( I have done well with Craigslist…you will be surprised who is renting out rooms to supplement their mortgages) – bring nothing but clothing and your car, if you kept it or take the bus. So the key is to work as many hours as possible while keeping your cost of living to as low as possible. I have friends who are nurses and they take 3 month “traveling nurses” contracts that include housing and then stash the cash and return back to Italy. Think of other seasonal work you could do that includes housing.
Before or after my “winter job”, I go see my family and really get to spend time together- like several weeks. My Mom loves when I come, we get her whole ” Honey do list” for the year done in just a few weeks.” When you do extended visits with friends or family, offer your time and talents. You are home and can wait for a repair man for roof or A/C inspections. Offer to take the car for service and sit and wait, or take the dog to the groomers. I love to garden and paint, so I am happy to jump on those jobs. I call it visiting without mooching!