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What if he rents equipment from someone, paying a company name, like Santa Rosa Rentals, but it's not a corporation? Is he supposed to 1099 that company?

Yes, you need to issue a 1099, since it's an unincorporated company.

Per the IRS https://www.irs.gov/businesses/small-businesses-self-employe... here are the situations when you don't need to file a 1099:

You are not required to file information return(s) if any of the following situations apply:

You are not engaged in a trade or business.
You are engaged in a trade or business and
the payment was made to another business that is incorporated, but was not for medical or legal services or
the sum of all payments made to the person or unincorporated business is less than $600 in one tax year


Since the company is unincorporated, it doesn't fall under the 'incorporated business and not for medical or legal expenses' exception.

AJ
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