This is a declining market with 3 of the DC area jurisdictions recently passing legislation limiting how many days you can AirBnB a property, and limiting it to owner occupants only.

So what I propose may or may not work in your situation and is based only on the information you shared in your post.You and tenant agreed to a move-out date of January 1, 2019 with an appointment for 4pm for the final walk-through and handing over of the keys.  

Call him back, tell him you are ready to talk and say you would like 5-10 minutes to go over your proposal and how about Tuesday.

I am a beginning real estate investor in NY and was recently contacted by an NYC wholesaler proposing to work on a joint venture "wholetail" deal in Bushwick, Brooklyn.

The purpose of my discussion is to propose my helping hands and additional energy to assist anyone within the state and city/cities with their properties or even company.

Keep in mind that lease language can not contravene state legislation.

Not in any legislation I am aware of except possible CA.  

If this is the case then TAW is in fact M2M and all regulations apply as with a term lease.Not much help I know but hopefully a MA landlord will point you to th eproper legislation.

@Caleb Heimsoth Not sure if I know the mechanics of what you propose. 

If so you can then take them to court for additional damage costs instead of rent assuming your state legislation allowse deposits to cover rent.