Alberta is the most economically free region in North America?? 
It’s my impression that Canada has a rather more sturdy safety net than the US. It certainly did 15 years ago.
I have some purely anecdotal knowledge about Berkeley and Chicago. A friend of mine was an employee of a small Chicago business that failed last year. Municipal red tape was the least of their problems. Bad management decisions and procedures were more of a culprit.
Berkeley is another matter though. Navigating the barriers set up by city hall is indeed daunting. But there are alternatives. You can save yourself the aggravation and locate to one of 4+ nearby cities with less regulation: these include Albany, Richmond, Oakland and Emeryville: the latter city is really friendly. But there’s also lots of opportunity in Berkeley: you just need intensive knowledge of and contact with city hall. An Ivy League degree won’t help you: think of their regulation as barrier to entry, one that can be surmounted with extensive research or hiring a local gun. But once you’ve cleared that hurdle, there’s plenty of opportunity. Hey, it’s tough to enter the jumbo jet market as well.