You cannot depend on plowing for income.
I have been plowing for 5 or 6 years. The first 4 years were great. In fact, when I started, I spent $18K on a truck and plow, and billed $14K the first season, solo. The 2nd year was just about as good, truck was now paid for, and some money in my pocket. I added a 2nd truck and plow year 3 and 4, and got average snow, but the investment paid off well, and kept my employee engaged over the winter. I also do my driveway, my sister's driveway, my mother-in-law's, and an investment house, saving good money for me and mine.
Last year it snowed twice. Ouch. This year so far, it has snowed 3 times. Not good.
The thing is...in Massachusetts you need to plow because some customers want a year round service. They only want to get one bill from one guy they trust. If you don't plow, you lose business to "one-stop-shops".