About 18 months ago after not paying for four months, I restructured our agreement and had him sign a quit claim deed that I would file if he were ever more than 30 days late.Fast forward to this month, March 2020.  

I'd also ask for proof of losing the job (which she needs for unemployment) and filing unemployment.

If they are confrontational and refuse to work with you at all, then tack on your late fees, and tell them you will be filing for all rents, late fees, filing fees, and attorneys fees the second courts are open, and you will be getting a judgement against them, hit their credit, and garnish their wages going forward until you are made whole.

However, I do not know what the tenant laws in Mass are so it might be worth either calling a local office or doing a basic google search to see if their are any details such as needing something to be notarized, or if there is a specific state template that needs to be filed. 

Should I file an insurance claim?

I was told by my closing attorney (GA) I need to file with the Georgia Secretary of State as a foreign LLC in order to do business in GA.

You can collect rent in a different name, you may need to register the name with your LLC as a DBA - Doing Business AsIt all depends on your state.https://startupsavant.com/how-to-file-a-dba-in-pennsylvania

WE are asking that if they lost their job, we would like a letter form their employer for our file, i addition, we ask that they pay as much as they can at this time.

What does concern me is that a redemption request was filed back in January, before you know what hit the fan, so why haven't they complied then?

@Zulf H.If they are not working due to COVId-19, they can file for unemployment benefits.