My question involves an eviction in the state of: Massachusetts
I am leasing a 2BR apartment in MA (only my name is on the lease and utilities). I moved in with a roommate, who is now four months behind on rent, and I need to evict them. I offered the roommate a month-to-month written sublease with my landlord's consent, but they never signed it. I believe this makes them a subtenant at will under MA law. I requested a security deposit, but never received one (as the check bounced). On December 8, I served a 14-day notice to quit by personal delivery, since my roommate is never home during the day and I do not know their work address.
I believe I am now in a position to file an eviction case, but want to make sure I'm doing it correctly. I have a few questions on the details.
1. The roommate is broke due to long-term illness (had been on state long-term disability, but those payments dried up for a reason which has never been made fully clear to me). I agreed to allow them to live with me only on the condition that their disability payments and other support would allow them to actually pay the rent. If I file to evict, will they be able to argue in housing court that I am discriminating against them?
2. Since I delivered the 14-day notice to quit by hand, is there anything other than perjury which prevents them from claiming they never received the notice?
3. What standard of evidence is applied in housing court to prove the non-payment of rent? I have a spreadsheet which I've created detailing charges and payments, and can get copies of checks which have cleared and bounced. However, for the payments which were simply never tendered, I have no specific evidence beyond my bank statements which don't happen to indicate a deposit. Will that be enough?
4. I have been attempting to negotiate with them to get them to voluntarily leave before 1/31 so that I can bring in a new roommate on 2/1. To what stage can I "pre-emptively" take a legal eviction proceeding such that I can have them removed quickly if they do not vacate voluntarily, and do I have enough time to do so?
5. Given that they apparently have little to no income, is there any real point to filing in small claims court to recover the rent (I am owed nearly $2800)? I would desperately like that money, but if they are judgement-proof due to indigency, will filing accomplish anything beyond incurring court costs? In addition, what standard would I need to follow in small claims court for documenting a paper trail to prove the debt, given that the roommate did not sign the sublease I offered? Alternatively, can I make a monetary claim directly in conjunction with the eviction case in housing court?
6. If I have to have them evicted by a sheriff and their belongings stored, is there any way for me to recover those costs?

