There is nothing wrong with being empathetic about a person's situation if, in fact, it is a real hardship but never let rent lapse beyond a month because that snowball is going to keep getting bigger and out of control.

This is where my wife gets upset with me for being too empathetic, but given we are still seven months out and this is my first time doing this I wanted to see how unreasonable I am for asking for that much (first, last, deposit = $6K) up front so far away from the move-in.

It is totally possible to be a kind, caring,  empathetic person and still run a business in a manner that generates lots of $$$$.  

To charge or not to charge, that is the question...I'm trying to be less empathetic when it comes to most business decisions.

Its good to be empathetic but don’t get caught up in their situations. 

Be compassionate, empathetic and courteous...

(at least thats our story and we're sticking to it) They will be empathetic as they have seen it all and it will probably amount to nothing for you there.

I realize I'm not offering you any advice, but wanted to let you know that I'm empathetic to your situation.

When we get those moments, and we do, my wife listens empathetically with and talks candidly to the offending person, outlines expectations and reminds them that so long as they give us 60 days notice, they can get out of their lease. 

Or do something like a one time, $200 credit...not sure of the exact solution, but be empathetic.