Connect with the case worker for that tenant ensure you get a courtesy copy of notices they receive from S8 so you're in the loop about recertification dates, etc.Confirm the information above w/ your State S8 office but I can't imagine they won't allow you to charge late fees. 

Quote from @Ana Mills: The high quotes for the electricians will be way cheaper than having your handyman do it and it causing damage, causing a fire, or even worse causing a fire later when someone is living there and that person/persons getting hurt because of the work being done by an unlicensed worker doing the work. 

@Sonja Revells , after reviewing the agreement you uploaded, I realized it could be a bit tough to fight for your EMD due to these sketchy clauses.

This market has a lot of large families and therefore 5-6 bedroom rentals are in demand and tough to find.

Discussing these points can help you make a sound decision.I agree wit @Noah Corwick that permitting and construction cost make this a tough option.  

Even with my former partner (who was our 'PM / GC' on site for our projects), it was sometimes tough navigating the process, managing budgets and costs, and keeping everyone in line, including him. 

Tough love. 

Having said that, the best course of action is to tell the tenant what day and time the appointment is and explain if she wants to be there for it that's fine, if she can't be there, that is fine too, the workers will be entering her property without her being there.

Boston from what I've heard is very tough with compressed cap rates.

Tough call!