Be an empathetic listener and let them talk!

You could have just as easily given Smokey the 60-day notice and left it at that - but you’re being as empathetic as possible to this tenant.

I am excellent with people;I am empathetic, fair, and honest. 

Make ALL of your messaging (texts, phone calls, letters) personalized and empathetic. 

I feel I am a bit more empathetic than most, but I also undervalued the rent we could get for the unit if it was improved... 

It makes me very empathetic to those searching for quality places to rent…and as much as I love my market I am not so naive to think we are the hottest market in the US, what I mean by that is I would suspect this is even worse in hotter markets than mine.  

Because IF they turn into a nightmare, and even good people can, or something comes up in your due diligence after the fact, you likely will have a much harder time getting them out than to have said "you don't qualify" - in the first placeBe empathetic, take the time to efficiently get through your process, but think very carefully before  you make exceptions.

. :)Continue to be kind, be empathetic and watch your blessings grow exponentially!

Therefore you do find yourself in these situations from time to time.I like your empathetic approach to the situation but will caution you that no matter what, it's going to be you vs the tenant.

I am extremely empathetic and have dealt with a similar scenario.