As you can probably tell from my name I have been traveling around the World for a number of years looking at places to work from and call home. I am actually settled back in the UK now (perhaps that proves there is no where better for me, in terms of friends, family, familiar culture etc).
Anywhere here is my opinion on countries to emigrate to for webmasters..
SOUTH EAST ASIA
Very cheap, lots of fun, frendly people, great weather. Corruption is bad but this can sometimes work in your favour!
Great if you are a single guy, hedonistic kind of place but lots of political instability and many foreigners have become unstuck there. Its still cheap and broadband improving. Great food too and great healthcare, although you have to pay for it!
Like Thailand was, very cheap food and alcohol imports of western food, never seen a place like it. 3G infrastructure too which was sufficient for me. Very poor but friendly people, poorly educated in many cases. Dangerous? Well I always felt safe but you need to keep your wits about you!
Best thing: Business visas for $20 a month, and no time limits!
INDONESIA / BALI
Going to talk mainly about Bali as I have most experience there. Biggest minus straight off is the visa situation, having to leave every month or attmepting to get a six month social visa, which is not easy to get unless you have connections.
Bali is very cheap, great cuisines, all the home comforts and great surf too if you are into that. Good 3G infrastructure too. Friendliest people on the planet, non muslim, and like Thailand people do end up in trouble here, particularly anything to do with drugs!
AUSTRALIA / NZ
English speaking, great infrastructure, increasingly expensive.
It is very expensive these days, many British immigrants complain it costs more than home. Visa situation is not good for webmasters. Easier if you are a Nurse or Trades person to get a visa than an independent professional.
I think Aus is a great country but a very bad choice for webmasters.
Great climate (North of North Island) not too expensive if you avoid imports, friendly people, long term business visa doable but you have to employ locals, not sure why some said you don't!
Biggest issue is the isolation and sense of being a long way from everywhere, there is also a surprisingly high crime rate, bad road death figures and if you are from a vibrant place then you might find the cities too boring and relaxed. I would say better to retire or take a family.
Just a few other observations...
Canada has an extreme climate! If its boiling in summer and freezing in winter it is extreme! The southern part of the UK on the other hand has anything but an extreme climate, av. temps rarely more than 20C (sorry not sure of F) apart from winter and summer.
Having said that the UK is cloudy and dull a lot which makes it depressing, especially with short days in winter.
I would say most of Latin America can be dangerous, even places like Ecuador, Mexico and even Costa Rica can be dangrous. I would say the only places like Chile are more safe, but there again you have increased costs.
To sum up I am not sure the OP will ever find somewhere that ticks all the boxes, but if they do I would love to hear about it!