Comment: Probably considered "structuring" or something similar.

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Probably considered "structuring" or something similar.

The IRS considers most arrangements like this to be attempts to abuse the system.

The big red flag will be that he doesn't "provide services" for anyone else. Thus this will appear to be trying to mask an employer/employee relationship and an attempt to avoid withholding.

They don't care if you are paying everything they claim you owe, if you also aren't doing it the way they want you to, they'll still go after you.

It isn't about the money—it's about control.