Tallinn is a great place. I worked there for a week last month. Nice people. I stayed in Parnu last summer briefly, that seemed nice as well. However, as the OP says, it's a very different place to Sydney.
I'm curious what the red tape was like. Did you require a visa or work permit? How long/painful was the process? I take it you had a job lined up before you went, did the employer assist you?
Both Australia and Estonia are party to the Schengen agreement, what this means is that you are automatically granted a visa upon arrival in Estonia for a period of three months, I lined up professional contacts ahead of time with a view to work, but nothing has been nailed down in terms of work yet.
I'm not concerned by this because with my final paycheque from Sydney at the end of this month I have enough funds to finish my experiment entirely, so worst case scenario I have to go, but I'm ok. It would leave me two months to work on my personal projects which I've wanted for a while, and an unobtrusive, peaceful and friendly environment to do so.
That said, I'm totally open to working with people over here and in fact looking forward to it if it comes to pass, I'm just not staking my game on it.
Tallinn is definitely a nice place nowadays! If it does not work out for you, Helsinki is just a short ferry ride away and Stockholm is not too far either...but unfortunately both are quite a bit more expensive :)
Edit: That is, it is relatively simple to check for jobs in either location and even go to interviews while still stationed in .ee
Thanks for the tip, I must admit I find both those places quite interesting, of course it turns out harder to live there completely independently off my freelance revenues, but as you say if the wages are higher getting a "real job" again might be an option. :)
How was the Aussie able to converse with the customer service people with the state-run telcom? He didn't mention any knowledge of Estonian or even Russian.
You won't have too much trouble as long as you keep to the center of the city. As in pretty much any Eastern European country, anybody under the age of 30 can speak english more or less acceptably. And expect to get ripped off by taxies if you don't speak at least one local language.
I'm slowly trying to learn Estonian from the Byki software package, but as a general rule, anyone young can speak english just fine, and even old people (My landlord is 60+) have a passable grasp of the language.
Dealing with the phone company has been simple, they have a menu option from the Estonian main menu to choose English, and although not all their staff speaks English, they can understand you when you ask to speak to someone who can.
Oh? Because you live elsewhere in Estonia and would rather he moved there? Or because you don't want the secret to get out and be flooded by itinerate programmers?
Hehe, nope.. I have lived in Tallinn for a few years (during university time) and this place is a lot more nervewrecking than either Tartu or Helsinki in Finland.
Also, I had some friends over from Tallinn this weekend and we hit a nighclub last Friday - they were a bit amazed how relaxed Tartu is compared to Tallinn.
I chose Tallinn because of two primary reasons, firstly Rob lives there, and although I'm kind of an isolated person myself, I didn't feel comfortable living in a city where I didn't have at least one person extremely close to me, and two I went with the assumption that there'd be better quality of life in the larger city. I have since arriving however heard a few times that Tartu is quite a bit more peaceful and still has all the important stuff that Tallinn does so YMMV.
Most of the telecom and multimedia companies that I know in eastern Europe have someone ready to take your call in either English or one of the neighbour country languages. Same with banks. A bit worse as far as other services go (electricity, etc.)
I'd watch out for those icicles though.