I don’t know what you mean when you say he has a judgment against you, but then you say that same case is still pending. I don’t know what you mean...

Yes, you should do all things with respect to your business as a professional business word.

No people cannot borrow money with a promise to repay it and then refuse to pay it.

People get things stuck in their throat all the time. You have to allege that they did something negligent to sue

Without knowing the complete details there is no way any attorney can tell you whether you have any time left at all, let alone how much time....

It sounds like you have a public defender so you should discuss this with that attorney.

The police are unlikely to get involved and unlikely to consider this theft because you gave him possession and now he is merely refusing to return...

Unclear whether you would have to see the city or the trash company but you may have a claim against someone.

No they don’t have an obligation to do much of anything.

Yes. Most likely. No doubt his defense attorney already explained the terms of his probation to him, but he can ask his attorney again if he forgot.