I'm going into my fourth season this year with the same guy.
He gives you the option of paying in two installments for a little more money, or all up front, for a little less. I have always paid for the whole season upfront and crossed my fingers.
The first two years he was great...the driveway was always clear when I went out in the morning at 7:00am, and he would be back in the daytime to blow the end of the driveway after the plows came before I got home. Of course, the snows were pretty light those years, and I'm sure he made money.
Last year, the service wasn't quite so efficient. Of course, it snowed a lot more in 2007/08, and I think he lost some customers on my street because his prices were always a bit higher than most other guys. So, he probably put me on the route to do last.
However, the one time I called him because it was imperative I had the driveway cleared because of a 6:00am flight out of Pearson, he was there at 2:00am to make sure I could get out.
I'm pretty sure he will be looking at asking for a price increase for this season because I'm sure he must have lost money last season. Having said that, I wouldn't want his job for "love nor money".