Usually when you get these early season snowfalls, it's slushy slop and near freezing. It's well below freezing right now. The snow is fluffy, icy powder. The ground was just warm enough to melt the first bit of snow into black ice. Your no-season tires are hard as rocks because it's bloody cold out. The roads weren't salted (nor should they have been based on the forecast, IMO).

People also generally lose their fucking minds around this time of year. Sunday Christmas shoppers are a pox. Live around one of the big malls and you'll become a grinch within a week. All these Mercedes SUVs being driven by a sentient bottle of Xanax...

We've had two very mild winters with a couple big storms that everyone worked from home for. There's literally millions of transplants at this point, that learned to drive in China or Florida, and have no idea how to drive in snow. Massachusetts drivers are currently about as trustworthy at driving in snow as your average Atlanta driver. The road surface also resembles those Atlanta snowfalls we love to make fun of: dust on crust. Abandon all hope, ye who enter here.

The plow drivers should go on strike soon and let Darwin clean this mess up, if you ask me. We need another Blizzard of 78 event where people have to abandon their cars. Too many people have lost their respect for mother nature...

You should really talk to a housing lawyer in Massachusetts. Most of the time, they'll give you a few minutes of their time for free if you call for a consultation. I did this once after I was in a car accident -- very helpful ~10 minute conversation on how to handle that, and I didn't actually need a lawyer in the end. https://www.usa.gov/legal-aid

This situation you're in is a bit of a grey area, as you've found. Ignore the politically motivated trolls whining about how tenant friendly MA is. He's not a tenant. Worst case scenario, he's a lodger. You're not a landlord, you're a homeowner with a deadbeat roommate. Best case scenario, he's merely an unwanted house guest and you can get the cops to remove him for trespassing if he doesn't leave. A lawyer would help you figure out exactly what he is and how to remove him legally. The definitions overlap somewhat.