You can find blog post from him where he shares his experience after one week and one month

That said, their Digital Nomad visa application was entirely digital, and didn't have clear options for someone who didn't need a visa to enter the country/enter without invitation. As a Canadian passport holder, somehow this made it more difficult to fill out and understand. I ended up with a lot of null fields when I filled it out. Would have had to stop at the local police office to finalize it, given the issues I had.

As for the experience, downs:

  - Cold+wind.. Not as cold as Reykjavik or as windy as Helsinki, but when these get together in Estonia, it's the worst.
  - I definetely miss socializing, especially when compared to countries like Spain or UK. Less interaction makes a less pleasant day and even less pleasant hospital experience.
  - As Estonian's doesn't socialize or talk much, it's much harder to learn the language by practicing-living here
  - Many brands or services not here. Estonia is usually one of the last countries in EU to receive some brands or services. Ie Apple products, official Apple store, HBO+. 
  - Also not many options for global companies to work
  - Travel options are limited. Flights are longer, more expensive and less frequent. 
  - Maybe few other things that I cannot remember atm

  - Digital mindset and almost non-existent bureaucracy. Both gov and private e-services very fast, transparent, digital, accessible. So far, I've done many I've applied for a bank account, multiple university applications and admissions, residency permit and driving licenses renewals, employment and rental contracts etc. 
  - Nature and silence, even in the middle of the city. 
  - Trust in the government, police and legal system

The country is divided between Russians and Estonians, and foreigners. Estonian politics revolve around picking on Russians. It's sometimes a bit comical: Estonian schools don't have enough teachers for Estonian speakers, because of lack of planning and funding, and now they want to ban russophone schools. Russophones are forced to "learn the language" (one of the most complex in the world) while being soft-excluded from the society. Anyway, Estonians don't really enjoy speaking with less-than-fluent Estonian speakers and will switch to english or try to make humiliating corrections, so picking the language is quite hard here.

People won't hold the door if you have a kid in the arms, doctors won't be nice to you, there's absolutely no culture of service. You have systematically to send emails, calls, in-person visits to get things done, or get paid. It's not me being nice, every local will tell you the same thing we he stops pumping the "Estonia is nordic" meme (it's not, it's a post soviet society with 0 public services).

Advice: don't go to Estonia. It's no wonder one fifth of the population already left.

My main complaint is that the remote worker visa gives you the right to stay in Estonia...and nothing else. You don't get an Estonian ID which is necessary for all sorts of things like setting up internet, getting a local phone number, or getting books from the library, and you can't get a bank account to pay your rent. LHV, Coop and SEB all claimed I could open an account with just my passport and lease agreement, but denied my application (after paying several hundred in application fees). The e-resident card is basically useless.

The tax situation is unclear. You become a tax resident when you stay over 183 days. But all US citizens are tax residents of the USA, so the USA-Estonian tax treaty kicks in with its tie breaker rules. Because I have a house in the USA, it means I would be treated only as a tax resident of the USA, so I would only pay taxes there...I think? But I can't imagine why Estonia would offer this visa program if they weren't getting something out of it.

It really is a beautiful country. And today is the first day of snow :)