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If a tenant has moved out and has requested all original and any copies of all documents that we have on him in his file, are we legally obligated to give them to him?
No, your records are yours; you are not legally obligated to give the tenant originals or copies of any of your records. In a lawsuit a tenant would be entitled to obtain copies of anything in your records related to him (unless the record was attorney-client privileged), but you may use your discretion to comply with or refuse his request. You could say that you would be happy to make copies, if he reimburses you for the cost, or simply tell him, “No.” If you suspect that the tenant is trying to set you up for a lawsuit, you may consider contacting your attorney first and review all materials before voluntarily giving any copies to the tenant.