Coming to Canada for 6 months or 12 months to work? I think that is really easy; those visas are available at the border. All you need is a passport. If you want to stay longer, though, there's tons of red tape.

Boston -> Toronto here. It wasn't as easy as you might hope. My wife's employer paid for an attorney to manage the paperwork, which was pretty awesome. Total time to permanent residency: about 3 years. Since our residency was finalized within the last 6 months, the 3-year estimate is pretty current; I think this should be considered the lower-bound.

I can't imagine how it would work for a freelancer. In my case, I tagged along with my wife who had a formal offer of employment. If not for her employer, I don't think it would have been possible to get the work visas and ultimately get residency.