I lived and rented in Massachusetts for years. I have been through the small claims court in Massachusetts many times.
This is the way it is:
The Judge in small claims will decide the case on merit. It has nothing to do with housing court..it is a straight forward case of damages (lost rent, etc).
When you win that case in Massachusetts you will learn that those courts in MA will actually HELP you collect!! It is far better than in most other States.
If after 30 days from the time you get the judgement they have not paid you..then you go back to court and file against them again..this time "to show cause why they should not be held in contempt of court for the failure to obey the court order". If they fail to show up, or again fail to pay as ordered..in 30 days, you go back to court, get the name of the local Marshall. Pay the marshal $50 to drag their deadbeat butts into court (in handcuffs if need be!!! it's great!!). I have seen judges get mad and put them in handcuffs right there in court..telling them that they will sit in jail till they pay me. (Funny how they find the money in a hurry then!).
I love Massachusetts small claims!
Has nothing to do with housing court...simple justice is handed down in small claims.