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Can my landlord ask me to write my rent check to someone elses?

No. The company name, landlord name, payee name and address, rental property address, rent amount, deposit, and your name must all be listed in the lease. I suggest you have the landlord add an addendum to the lease with verification of the payee and address. Have him write you a letter with the company name, address, and payee information. You must retain this documentation. Make sure you receive a receipt for each transaction as well, or that can see the financial update on the companys tenant portal (if there is one) and retain personal copies. I am not saying this person is purposely being deceitful. However, he could be trying to evade paying taxes on the rental property income. That in turn could put you in the middle of a fraud case with the IRS when you file taxes. I simply would not take the chance. Additionally, without proof that your payment made to this third party is even involved with your rental property, the landlord could come back at some point and say they never received payment and evict you; thereby, finding a way to keep your security deposit and sue you for rental funds already paid.

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