@Anders Rodland -thank you. Yes, I agree, I hope that he moves out without major damage. We have had a good relationship over the past 1.5 years, and I have really bent over backwards to help him after he lost his job. Hopefully that all wasn't for nothing!
@Jeff B. - Thanks Jeff! My name and the word bright don't get thrown together all that often! haha. I hope it all works out for both me, and the tenant.
@Chuy Gonzalez thank you for the advice. I already have the lawyer ready. Just hoping we don't have to make that call :)
I have to admit, in the less than two years I have been a landlord(5 units now) i haven't really ever had to be the bad guy. I can already tell that is something i need to get more comfortable with. I was firm, but gentle when i explained everything to him. He was mad, but also understood where i was coming from. I felt "shakey" during the conversation, and sick to my stomach. But this was the right thing to do for my business--it had to be done.
The one thing that i have learned is that no matter how much help/kindness/generosity that you show to someone...it doesn't always matter, because they don't want/respect that. My wife and I gave all of our tenants a $50 discount for December, so they each had a little extra spending money for Christmas. Then, just over a week later, this happens. All I can do is keep on treating people the way that i would like to be treated. I feel like I will definitely win more than I lose with that strategy. Thanks everyone!