Only issue is to not go OCD with this approach as your sole effort to locate properties.

Tenant A has requested a new lease and to be the sole occupant of the unite so that Tenant A can apply for a utility assistance program through the State of Massachusetts.  

If this is the sole (remaining) grantor, then, yes, this type of accounting is likely necessary.

Of course, during your inspection, you will notice other things that are the tenants' responsibility, and point that out to them or even let them know you will be checking, but creating the inspection solely as a check-up on tenants could create an adversarial relationship that might cause problems long term.

If I were in your shoes and I would.

@Jordan Santiago@David Bokman   you should put your self in the sellers shoes here.would you like your mother to be treated this way..

We're looking into buying another home solely under just my wife's name (her "first residence"), so we don't tap out both our credit so quickly. 

I heard that I have to live in the property as the sole resident for a minimum of 5 years before I can consider renting it out.

you present the deal ( and it needs to be a real deal)then you close HARD FAST OFTEN.. if they him ha  its next. so I would if I was in your shoes..

However, if I was in your shoes, my first preference would be to partner with someone who had already flipped a few houses, the more experience, the better.