If I have 3 rent houses where tenants pay me rent directly but I pay the property manager for management, labor and expenses, should I issue a 1099 to him for that money?

[DS30 · Accepted solution]

It depends - If the property manager is not employed with a property management company but works as an independent contractor, then you will need to file a Form 1099-MISC if you pay him more than $600 during a calendar year. If the property manager is an employee of a management company, then you will have no Form 1099-MISC filing.