While you're out in the field make notes of properties you like that aren't being maintained - look for high grass and weeds, broken windows or unshoveled snow in the winter.

And with that much incessant demand coming down the pike every day, there'd be plenty of lousier options mixed in with those secondaries.

A private driveway doesn't have to meet those standards, but also doesn't get public snow removal or public repair. 

Lawn care/snow removal

Your gang of thieves (and it would take a gang) might have better odds  of success knocking off armored cars at high noon or kidnapping wealthy children for ransom (a crime with a near-zero success rate in the developed world today).Get the case number, contact the USPIS independently, see if this rent heist story isn't really a snow job. 

I have flipped a good amount of houses like this one (without the snow issue lol).Get 3-4 different contractors to bid the job and then get started on it ASAP.

Obviously, in Connecticut it snows during the winter.

Only one tenant has ever abused the situation and called and texted incessantly.

There is one town near Mt Snow, for example, that has an outright ban on STRs.

Or they trip and fall because the snow wasn't cleared on time.