you want my oppinion? Court won't solve the problem because they can't MAKE you give money if he really doesn't have it. Fighting him over it or damaging his personal property won't get anywhere and just puts you at an even lower level--intentionally damaging someone's property would eliminate any recourse you could have had in court Vigilante justice died in the 1800's anyway.
Actually, there are options when you don't have money and a court orders you to pay . . .
You can garnish wages, put a lien on property, etc . . .
And, if all that fails, they get to learn the meaning of "contempt."
The rest of what Cody said is dead on. If "Bob" stoops to the level of destruction of property, or violence, "Bob" will find NO sympathy in court, and will be SOL (and probably a SOB).
My $0.02:
What occurred is called "conversion of property," and it is justiciable (you can sue over it, and win).
I don't know you'll find an attorney to take the case over $300, but you certainly can file a complaint yourself in small claims court and probably win.