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Paperwork, proof and a pad

The sudden application appointment was both a blessing and a curse, since it meant she had only 10 days to get her documents in order and find a place to live in Italy. Thankfully, her father, who works in real estate, was able to help her find an apartment — though she had to put down a deposit of three months’ rent without knowing if she’d be able to move there.

She also bought health insurance, secured documents proving she’d been working remotely for several years and compiled her tax returns and client contracts from her past employer and current clients.

She had her degree certified and, although it wasn’t required, she also provided criminal background checks. The minimum income to qualify for the visa is about $27,000, but Waite told CNN that she’d heard it needs to be three times that to be approved. In total, she took 120 pages of documents to her appointment.

Ten days after her appointment, she had a visa.

“By nothing less than a miracle, everything fell into place,” she told CNN.

The digital nomad visa lasts one year, at which time it can be renewed for a permit to stay. It takes five years to qualify for permanent residency and 10 years before you can apply for an Italian passport. In accordance with the visa, Waite now pays a 5% flat tax rate on her income to the Italian government in addition to paying some U.S. taxes.

She believes the entire process cost her between $5,000 and $10,000, including the visa application fee, degree certification, background checks and apartment deposit. But she is saving $1,500 a month after trading in her “astronomical” one-bedroom apartment in San Francisco for a two-bedroom apartment in Milan and, according to livingcost.org, the cost of living in Milan is 43% lower than in San Francisco.

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How to make a similar move

If you’re thinking of making a similar move — to Italy or elsewhere — you should be prepared for a similarly arduous and costly process. Many jurisdictions offering digital nomad or remote worker visas have similar requirements around income, experience, accommodation and criminal background checks. You’ll also require documentation to back up your application, some of which may need to be certified.

Beyond the application process, there are other administrative considerations that will require time and effort, like taxes. You’ll need a thorough understanding of how taxes are paid in your new home country and what you’ll still need to pay to the IRS.

You’ll also need to set up a bank account that can handle international payments. There are several online banks that accommodate multiple currencies, but you may want to consider an international bank with branches in the U.S. (be prepared for hefty currency exchange and transaction fees, though).

You won’t want to forget about health insurance, either. Your current travel insurance provider may be able to help, but you can also search online for a policy designed specifically for digital nomads.

After all that, you’ll need a place to live — along with renters insurance. If at all possible, get help from someone in the location you’re moving to. If this isn’t possible, check online forums and do as much research on both the area and building that you may be securing. If you can swing it, you can also ask to put a clause in your contract allowing you to claw back your deposit if you aren’t granted a visa.

Today, Waite lives in a chic neighborhood in Milan, runs her business remotely and takes weekend trips around Italy. While relocating takes a lot of time, money and effort, living the life of a digital nomad can be well worth it.

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Vawn Himmelsbach Freelance Contributor

Vawn Himmelsbach is a journalist who has been covering tech, business and travel for more than two decades. Her work has been published in a variety of publications, including The Globe and Mail, Toronto Star, National Post, CBC News, ITbusiness, CAA Magazine, Zoomer, BOLD Magazine and Travelweek, among others.

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