However, I've been standing on the sidelines for far too long - time to make it happen.I am a lawyer by training, and spent some time as an Air Force Judge Advocate or "JAG" (a military lawyer, for those who haven't seen the TV show), and transitioned into the federal government in the field of information privacy/security. 

You  should find out if the tenant actually has some kind of interest to go after.You can hire a lawyer and pay him/her however much they ask.But after the judge makes their decision to put a judgement on the tenant for the amount of rent unpaid they actually dont even have to pay it.It will hit their credit score and that is it and as we all know people who rent dont really care about their credit.I also dont beleive you can evict a tenant in NY if they are currently paying.

The bank had filed a summary motion in Circuit Court, the people living in the property filed a answer to their motion, and the judge ruled it would go to trail.

Who do you think a judge is going to believe ? 

@Steve FitzgeraldIf you did not specifically point out they were not included or said if they break down they will not be replaced a judge would probably rule in their favor regardless of the law.

@Chris LeMayI’d be careful on this one...I don’t think the judges in my area would allow keeping the deposit.

It also creates more work to have a dialogue, rather than just make a declaration.  

Will it be more heavily judged on the experience of the asset manager, or the potential return, or the type of property?

That’ll piss them off, they’ll stop paying $100/day, stay there for the next month ($3000) until your eviction process and makes its rounds through our courts.The judge will say you collected $100/day...which sounds more than fair.

But I also know that part of it comes down to my property manager being an excellent judge of character.