the best time to buy would be right after the winter season when all the shops are trying to clear their old stock. if you could wait id suggest letting this season pass and buy one shortly after the last snowfall. if you cant wait then try buying during fall when the shops are still trying to clear their old stock to make way for the new ones. just dont wait til the first snowfall since that would be the worst time to buy one.
Not trying to be a wise-guy, but the time to buy is when you don't need it.
Buying after the season is probably the best bet for a good price, but the choices are somewhat limited in my area.
It seems like the most desirable models, (for me), are hard to find at the end of the season.
Don't wait until the first snow or even the first forecast of heavy snow. Everyone needs one then. I have even heard of some dealers raising their price in those times.
Thats what a lot of people told me. I really want to grab a new one for this season though. So I might buy one pretty soon depending on finding the right price for one. I might even try to find a good used one and just repair/restore it if needed.