I agree with both of the attorneys above. But please keep this in mind, if the judge feels that the matter could have been avoided by a "proper" payment on your behalf, he/she could award attorney's fees.
Court-ordered restitution must be paid in order to satisfy your son's probationary requirements. However, your son may demand that the amount in question by proven by the complaining witness in this case. However, if the Court determines that there is sufficient evidence to support the claim for $5,500.00, your son will be left with very few options.
If your landlord gave you the requisite time before he had a court officer remove your belongings, you will not be able to sue. However, if this time frame was breached, you may be able to file suit. Based on the information you posted, I lack sufficient facts in order to form an opinion. The time frame involved is very important in determining the answer to your question.
Absolutely. However, this is a matter for the local police department. Outside counsel will not be required.
When dealing in this area of the law, a lot will depend on what is in the lease agreement that you signed with your landlord. However, if the lack of repair rises to a dangerous level, you could proceed with a constructive eviction and withhold rent until the repairs are completed. Hope that helps.