Posted 16 April 2012 - 17:56
As Brad and others mentioned, you should not be naïve about this (I'm Canadian by birth).
WORKING, PART 1: Since Canada is a foreign country from the USA, you are obligated to follow every immigration rule the US Government has ever conceived. This includes work visa paperwork and approvals, sponsorship arrangements, temporary immigration paranoia (read: instant deportation by DHS is 100% permissible), and double taxation (Canada doesn't care where the money came from... as a Canadian citizen who spent part of the year in Canada; likewise from the American standpoint).
WORKING, PART 2: The "best" way is to keep working in Canada, virtually, as an independent business. This establishes a relationship with a potential corporate sponsor who can apply on your behalf within the USA and justify your necessity whichever way works in their best interest.
LIVING, PART 1: The Canadian dollar is pennies stronger than the American dollar, but the culture is aimed towards instant gratification. You keep more of your paycheck upfront only to pay Uncle Sam (annual income tax) at stringent rates... and things like Social Security, Medicare/Medicaid, state-level income taxes, city-level income taxes, personal benefits, personal health insurance premiums, ongoing costs of living, etc. At the end of the day, you net out with more instant-gratification but less long-term happiness.
LIVING, PART 2: Cost of living in Metro San Francisco, Metro Boston, Metro NYC, Metro DC... is about 3-5X cost of living in Toronto or Montreal. Period. A basic 1-bedroom apt in NYC costs $2500/mo in rent alone, and that's in Manhattan without a doorman. Want buy a condo? Try $1.5M for the same unit. Brooklyn provides better rates, but "better" is extremely subjective.
LIFE: International quality-of-life indexes have indicated, for the past 20 years, that any major city in Canada is ranked MUCH higher than the top US city.
FAMILY: Once you are an established temporary resident, your family can visit. Once you're an established permanent resident (green card) or citizen, your family can move with your without any problems. Canadians are notorious for overstaying their temporary visitor visas, and the penalties range from financial penalty, multi-year travel bans (for anything and everything), to being permanently being banned from the USA or its territories (including Puerto Rico).
OTHER: Generally speaking, if you have favorable ties to Cuba... keep it to yourself 110% of the time. It's the easiest disqualifier the US has against Canadian citizens.