Crazy, you're in the exact same boat as me, small subdivision just outside a big city, self employed software developer thinking about making some beer money and having fun doing it. I decided against it for several reasons. Liability has been covered above and so has insurance, but for me, there was also the problem of being tied down on the weekends. My wife is from Toronto (5 hrs away) and we travel for Christmas and a few birthdays over the winter. Going down south for a week or taking the kids on a ski trip would also be out of the question.
As others have said, not everybody is going to be reasonable, or at least on the same page as you when it comes to how often and when you'll be clearing snow. You may work from home, but you might not want to get up at 4am to get them all done before people are trying to get out for work.
Another thought that stopped me was the problem of equipment failure and how to handle a couple dozen driveways if the tractor or blower was down for a week.
In the end I'll end up helping a few of my friends/neighbours when we get hit hard, just to be a nice guy and for the enjoyment that I get from seat time. Reduced liability (my insurance covers me as long as I don't make money), no complaints or demands, no commitments but unfortunately, no beer money.