If you do confront him, which it sounds like you really want to, bring a witness. 

When I started out and was doing it myself, I had a county return my assignment twice - one because there was only one witness instead of two, the other because of not enough margin or something like that.

BTW--a two year lease must be witnessed in the State of FL.

You think you might be witnessing drug use on the front stoop.

. - I think marks would  fall under general wear and tear.You might be able to charge for cleaning if the apartment wasn't returned in the same clean condition if your lease provides for it.Make sure you also account for the interest due on the deposit. ( In CT ) if you don't provide the itemized deduction and interest credit wit in 30 days you could owe the tenant double the security deposit.

I have witnessed how this has paid off for him.

We work exclusively with investors which makes it a great fit for me to learn everything I want to know and witness it happening.

After other gentleman's car lost in court they appealed and hauled me in as a witness.

If you witnessed the break-in, they may do something about it.

@Nathan W. it's always a balance/choice between amount of insurance and LLC for asset protection.One thing everyone forgets though, is keeping your name out of the equation also keeps you & your family personall safe:1) Not nutjobs tracking you down and showing up at your house (happened to me)2) Keeps your name out of the news if something goes wrongFYI - not sure why you and Edwin both show separate Management Companies?