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Recovering a security deposit in Boston

I have been reading though the posts on recovering a security deposit because I am anticipating that our landlord will not be returning our security deposit.

The situation:
In 2007 we signed a one-year lease. The landlord lives above us with her kids.

The landlord collected a security deposit. We never received a receipt or any bank information. We have the canceled check and on the check we wrote "security deposit." Furthermore, we never received a "Statement of Condition."

In 2008, we verbally and via email agreed to stay another year and that all the same conditions of the previous lease would apply. Following this, we never renewed the lease in any manner (verbally, via email, in writing, etc.). Thus, our lease expired in 2009.

Starting in 2010, our landlord would be up at all hours of the night moving furniture, hammering, and making a ton of noise. Thus, preventing us from quietly enjoying the apartment. We nicely asked her to keep it down and she yelled at us saying it was her house and she could do what she wanted. This back and forth went on for several months. Eventually, we had enough of being woken up between 1:00 and 5:00 am. As such, we gave her 30-days notice. In addition to giving her 30-days notice on the phone, I sent her a certified letter and we have not heard from her for a week (except for the noise in the middle of the night).

In the terms of the lease it states it goes to month-to-month after expiration and there is no automatic renewal.

The questions:
If she does not return our security deposit within 30 days of us moving out can we sue her in small claims court even though three-times damages would exceed the $2k limit?

Can she claim that she is unable to attend the court date due to her job and forever push back the court date?

If we go to small claims court and win, can she still refuse to return the funds? What is to prevent her from just NOT returning the funds?

Thanks

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