Is he mentally disabled ?  

Report each issue on a separate ticket (grass, trash, health hazards, etc).

Simple solution: Inform them that unfortunately you can’t accept ESA letters without being able to verify the validity of the letter by speaking with the local licensed mental health professional who prescribed them their ESA, so that you can verify that they have a legitimate disability requiring an ESA as well as that whoever prescribed it to them is a real licensed mental health professional who has an ongoing relationship with them beyond just receiving a one-time payment to “prescribe” the ESA. 

For our clients, we separate repairs into catergories: 1) Health & Saftey - highest priority to avoid lawsuits2) Property Preservation - don't want a $500 water leak repair to become a $5k repair later3) Government Required - for city & S8 inspections4) Marketing Negative Impact - who wants to rent a "purple" house?

One other MA change on the health care side is they have lowered lead levels of children on which action from the state will be taken in MA so more people with see health department intervention earlier that has it upsides. 

I asked my roof contractor to remove the skylight and replace it with a normal roof as well (which he did a few days back).My tenant is saying to the PM that he is getting medical testing done now due to mold related health issues.

About 90% of the time they fail to meet HUD guidelines.HUD guidelines require that to qualify as an Emotional Support Animal, the prospective resident must have a letter from a licensed health professional, licensed in your state, in which the health professional acknowledges they have a relationship with the client that was more than just one session. 

@Andy OkamotoOne cautionary note: if your idea of "cash flow" is $10K in net operating income, $120K before taxes in your pocket every year off your rental property, well, if it happens to you in 10 years, it will be a low-probability event with a lot of lucky breaks and eventually will likely ruin your life when you make a misstep because you assumed your lucky break was the norm.If you're serious about moving out here, at least look at the Pittsburgh area and its proximity to Carnegie Mellon (tech) and UPMC (health care).

With ab1482, we do not do rehabs beyond health and safety.  

If you want a feel for demand in Boston area there is a FB group boston travel nurses/health professionals.