The MA rules for handling of the security deposit are very restrictive (read that as overly ridiculous) and mishandling of that deposit routinely results in triple damages to the landlord. 

When I say I have been at this quite a long time, it is absolutely true, because I have logged more hours in the Courtroom than most of my colleagues in my particular peer group.But that is besides the point, because nothing about that changes the nature of the information I am providing.I have routinely argued and had upheld, in my jurisdiction, attorney fee provisions for 25% of principal owed.

Even then, the “big boys” playing with leverage in the markets you mentioned routinely run into issues using leverage.

Some great books that will help are: No brainer, "Rich Dad Poor Dad" changed my life and how I think about money now,"The Miracle Morning", having a routine in the morning was the best thing for me. 

It is routine to get potential client information (to ensure an attorney isn't adverse to the potential client on another matter) and to get information on known adverse parties for the potential matter of the potential client (to ensure those adverse parties aren't existing clients) prior to accepting a client.Furthermore, taking on a client without checking for conflicts may cause the attorney or firm to have to get rid of existing work they have for existing clients.  

Couple of the things that have made my life easier as an owner and property manager:Listed out tenant qualifications in our application processCreated reminders to do routine checks on properties (check HVAC, clean gutters, etc.)Leveraged property management software (we use Buildium)Thanks again for starting the conversation!

My property manager will email me a heads up for routine repairs that they don't even need authorization for out of courtesy.  

I love to watch stand up comedy but so far no one has done a routine about "games tenants play" and what happens when landlords uphold their rules.

If they are newer or routinely late on rent....sorry not my problem!

THE SECOND MONTH Somehow during the Second Month, when the newness wears off and the happiness falls into a routine, the new Tenants become confused.