I'm not in MA and I'm not a lawyer, but I know a little about HOA's and Condo Associations. First, if you live in a condo, you are part of the ownership of the parking lot and common areas. Associations set up a budget based on what they believe it will take to allow normal operations. When things go well, they develop a surplus. When they don't as in the past winter, they run a deficit. Someone has to clear the parking lots and walkways. That costs money and if the funds are gone, someone needs to raise the revenue to cover the costs. The alternative would be to have had the cars all stuck and the walkways all impassible.
I'm just making some intelligent guesses based on how Associations generally work and the winter the northeast has just been through.