Look, I get being empathetic and all, but this person is telling you I am in financial distress but they want the property owner to solve that problem.

I think it's important to remember when dealing with short sales that the people are in a desperate place. be aware, and empathetic, but don't let them take advantage of you.

Be empathetic but be ready to walk away from a deal that doesn't make enough sense.

The last check I mailed to them in November was returned to sender as undeliverable by the USPS.I am empathetic to their situation, but I want to make sure that we are dotting our i's and crossing our t's. 

You can be firmly but fairly empathetic.

From my experience, if you approach the conversation in an empathetic, considerate way, tenants generally respond positively.

I hope to tactfully and empathetically talk to him about his current condition.

Tenants have asked me to do this in the past I reply, empathetically, sorry I can not do this. 

I think the most important thing is being empathetic to their situation. #1 because it's the right thing to do during these tough times.

AND then be super polite and empathetic and service minded about how you get them to fix or get them help to fix the deficiencies, OR be a hard-*** if that's your preference.