If anyone is interested in some specific numbers, I can provide my own for my city.
Over the last 8 years I've lived in four apartments in Vancouver. Moving is a bit annoying, but not too much work when you have limited stuff. It probably helps that I don't set my mind on moving into a specific building and resort to going homeless when they don't have a convenient opening (Seriously? Why would someone do that?), but that's besides the point. Pretty much any city has some combination of Craigslist, bulletin boards, phone books, and internet access, which is all you really need to find a place.
My rent has gone from $600 + utilities (about $50/month) + transit pass ($81/month at the time) to $755 including utilities, + 1 book bus tickets/moth ($21/month) over the last 8 years, though the last two apartments were a SIGNIFICANT quality upgrade from the first two. My only housing-related additional expense is mandatory renters insurance, which is $15/month.
The cheapest, smallest condos in the city start at around $250,000, + utilities/garbage/sewage/whateverelsethecitycharges, + MUCH more expensive insurance, + $200 at least in strata fees, + maintenance, etc etc. The second you have something serious that needs to be fixed with the building, bam, special levy, for pretty much any amount - my boyfriend mentioned a building he knows of where it came to $100,000 per unit, all at once, for major critical work.
Mathematically, I just don't see how you could possibly come out ahead by buying rather than renting here.