(chronic non-payers for the previous landlord).

My thing is, we are still getting to "get a feel for each other" and I don't want them mistaking my kindness for weakness. 

That being said, B is fairly weak too.  

As I explained to them, I would rather weed out the jerks on the front end with a tough app vs. having a weak app and having to deal with evection, especially dealing with tenants in Chicago.

All 3 options are weak. 

The court case contradicted what I was told in training.I tend to agree with Sue that the enforcement is weak and having a confused organization would make it even harder for them.

My fear is that this sets a precedence, that management is "weak".

I wanted to share the solution that I put in place to manage our properties while we're traveling, and I'd love to hear some perspective about its strengths, weaknesses, or alternatives.This solution was really put to the test and passed when I was unreachable for days in the bottom of Palo Duro Canyon and a hot water tank popped off in one of the houses. 

If they can't pay it up front then they are a weak tenant and you should keep looking.

Also, tenants with a chronic mental illness are permitted to have emotional assistance animals." --- NY Civil Rights Law § 47.