Ethical behavior and business practices are important as well. 

I would talk to him (if you're comfortable) and let him know the behavior is unacceptable, that you are concerned he may end up in jail and unable to pay rent or stay, and it would be in everyone's best interest for him to leave now rather than be forced out.

That kind of behavior means they cannot be trusted.

Because as the poor become more and more impoverished, they tend to forget they're temporarily embarrassed millionaires and realize they're POOR, and their behavior becomes unpredictable.

@Matthew Orton I've been doing student rentals for 15+ years and the only thing that I've found that can sway difficult student behavior is through a fine.

I may suggest a delay of onset to October as a gesture of goodwill, but my concern is I am rewarding the behavior of challenging and negotiating my rent increases, and looking for “compensation” for every inconvenience that comes their way.

It’s remarkable that the Austin metro’s pricing is nearly 40% higher than it was last year:Despite the incredible YoY increase in prices, the decline in closed and pending sales compared to this time last year suggest, in light of the previous month’s numbers, that the market has found a stabilization point and may be reverting to its more predictable seasonal behavior.

Right back to the top post in the forum.These two behaviors make browsing the forums very frustrating. 

In the same way, if another child brings a toy and doesn't share it but it flaunting it at other children, I talk about how that is actually his toy so he can do what he wants with it, but that his behavior is ugly and he is trying to make other children feel ugly, too--he is trying to make then envious, and why it isn't his owning of the toy that's the problem but his nasty behavior and how we can avoid being dragged down with him, etc.I make sure my kids both succeed and fail.

You subsidize the behaviors, you get more of them.