rogerd - 9:25 pm on Aug 25, 2010 (gmt 0)
One aspect of life for a "work at home" Web entrepreneur is the ability to hang out with people in the same business. Online interaction is great, but it's nice to chat over a beer, too.
I just moved within the US, from northern Indiana (horrible winters, though nothing like most of Canada, upstate NY, Minneapolis, etc.) to Austin, TX. Hot summers, very mild winters.
One of the best parts of the move has been the large population of tech and professional folks here. Meetups that would have drawn three people in my old city draw 200 here.
In short, "Community" wasn't on the list, but I'd keep that in mind. It's a plus to be able to hang out with people who actually understand what you do.
In US locations, one key consideration are state and local taxes. In some states, these can amount to more than 10%, with New York and California being some of the worst. Texas, Tennessee, and Florida are among the small number of states which don't have an income tax - that's a big difference. Housing in those states tends to be a lot cheaper, too, though costs vary by locality.
I spent a year in Mexico a long time ago, and would have recommended it as a possibility on most of the requirements. At this point, though, I'd wait to see if the drug violence abates, or find an area that seems more or less immune.