My question involves landlord-tenant law in the State of: Massachusetts, city of Boston
My husband is a landlord and keeps having issues with three tenants paying rent by the first of the month. All are 30 day tenancies; two are lawyers. Massachusetts and Boston have a 14 day notice to quit; in other words, the rent has to be late by the 15th day in order to serve with eviction for nonpayment of rent. The problem is, they all get the rent to him by the 13th or 14th which, although late, is not grounds for eviction. He has sent letters reminding them that rent is due on the first, made copies of the postmarks on the envelopes as well as the dates on the checks, as well as calling them to pick up the checks (that supposedly have already been mailed). Things change for a month or two then we are right back to the 14th again. We can't charge late fees because that's illegal in this state. He could give them 30 day notice since they are not on leases, but would need to stagger them as each apartment probably needs work and two empty apartments in one building at the same time would be financially difficult for us to maintain for more than a month or two.
Any advice or can you direct me to texts that might help? While I think I'm pretty well versed in the rental laws here, and I do think it will come down to giving 30 days to one of the renters first, I can't seem to find out what other remedies we might have in both the state and the city (which is super duper tenant friendly). None of the three are Section 8s or assisted; as I mentioned two are pretty well established lawyers and each are at least 6 plus year tenants. All the units are a little under market value but are well-kept and maintained. Thanks for any input you might have.

