When I am traveling - for business or pleasure - the last thing I want to do is scramble to figure out where I will sleep that night. I value my time too much, especially for a pleasure trip, to go through that kind of ordeal.
Also, you can save money if you pay in advance for your hotel. You won't have time to even comparison shop if you're rushing at the very very last minute.
So, I wouldn't say the risk is overrated, but instead that people can stomach different amount of risk.
I like to be well prepared and have firm plans on my trips, but I know other friends will just book the first things they find and figure out what they're doing when they get there.