I vote for Orlando. It meets all of your criteria, but here's some other benefits as well: 1. Direct flights to/from pretty much anywhere. 2. No state income tax. Tourism revenue makes that possible. 3. Close proximity to two completely different beach experiences within an hour and a half drive, Gulf of Mexico and the Atlantic Ocean, and both have excellent fishing and boating excursions. 4. A ridiculous number of excellent restaurants and entertainment options. 5. If you become a grandparent, your kids will bring the the grandkids to visit you because of all the theme park options. 6. A golfer's paradise if you're into that.
I can't believe that the obvious choice has not been picked already as the clear winner: http://cometotoronto.com/ (Personally, I'd choose Halifax -- my need for "culture" can be contained/salved by The Interweb. But away from the coast of Maine, you'd have pretty much any town on U.S. 2. -- all the way west to Ashland, Wisconsin/Duluth, Mn....... But that's jus' me.)
Checkout Florida, many NY firms have offices in West Palm Beach and Boca Raton. Stay away from Ocean and intracoastal homes, they can be expensive but that's relative. Compared to NY or LA, it's still cheap. A few miles inland the prices drop 75% or more if you shop wisely.
No way, and trade under canadian restrictions. The cost of housing is $1000+ sqft for a third tier city. Deal with currency exchange, 6 months winter and traffic. Everyone I know in TO has a florida winter home and a cottage to get away from the city.
I love Toronto, but it's even more expensive than Boston...and it's full of Canadians who voted for crying boy.
Live in a Seattle boathouse, -- I'd love to live in one of these, but I don't know how to swim. It would seem weird or dangerous or hypocritical to live in a boathouse...only to accidentally die from drowning/slipping. Make Trading Great Again 2018...High-Five`
I've been all over Cebu, it's a fairly big island. Cebu city is quite crappy and very polluted, only useful for obtaining imported goods. Souther part of the island is amazingly beautiful and filled with a lot of foreigners (mostly German, French). The problem is that Cebu city is 2-3 hours away, so frequent trips for say, food, are out of the question. There aren't any other cities around either. Lived in Japan and found out it's definitely not for me. I loved Japan as a tourist, as an almost-immigrant, I got very dark and depressive vibes. It's very modern but you definitely need to learn Japanese and if you want to own a car and a nice house, it gets very expensive. I lived in an apartment the size of an American clothes cabinet so it was not too horrible, price wise. Being born in the USSR myself, I wouldn't lump all the countries that were part of it together. I suppose you meant Russia, tongue-in-cheek. I find Russians and Americans to be very similar in most ways, both on average are very patriotic; both have very intelligent, rich, power hungry and ruthless elites and a huge amount of uneducated trash...and that's why they don't get along.