If you have skills in one of the many categories, and with 20 years in tech you should, get the offer. Once armed with an offer from a Canadian company you can handle the visa at the border. For Quebec-based companies you have to have a handle on French but for the rest of Canada it's a skills and education based system for getting permanent residency.

The wage difference for IT workers is often 3:1 or higher in the US economy, as Canada has 1/10th the population with higher ratios of university alumni.

Starting a business in the USA is often far more lucrative, but people usually still incorporate in both countries for tax and liability reasons.

Things like the Canadian youth tax-credits also mean anyone over 28 gets pushed down the list for entry-level positions. The US is far easier to find a reasonable job, and the cultural tradition of entrepreneurship is far better. =3