What is truly important, is the behaviors that you develop by setting and working towards those goals.  

Getting a judgment is feasible, but collecting will be difficult.Clearly, the tenant is irresponsible just based on what you have disclosed.The pattern of behavior exhibited by the tenants leads me to believe you'll have a hard time getting any money regardless of the route you pursue.Personally, I say you negotiate with the tenant.

They should be on their best behavior now trying to get a place.

I guess this comes down to more a human behavior discussion which is beyond what I really wanted to get into.Maybe I am just lucky but some of the agents I have been involved with have said some pretty crazy things to make sales.

Their current behavior is either based on a lack of willingness or a lack of ability.

Clearly articulate your expectations and give them three days to alter their behavior.

If you expect a fast response from them, then you better show the same behavior in return.

The process is centered on behavior, structure can be argued, but only as mitigation.2.)  

Additional proof could potentially be my past behavior. 

You could implement new tenant rules that ban whatever behavior he is accused of doing, then serve him notice that he's broken the rules (following state law), if he doesn't correct, you move to evict.