@vgentry wrote:
So let me ask this question. If I send up to $600 to him and another up to $600 to his mom is that ok?
Note that the filing requirements and the requirements to issue a 1099-NEC are different. The teenager is legally required to file a tax return if he earns $400 or more for mowing lawns, whether or not he gets a 1099-NEC. If he earns more than $432 he will have to pay self-employment tax (but not income tax, unless he has other income). If he makes money mowing other lawns besides yours, or from any other self-employment, his filing requirement and his tax are based on his total income from all of his customers, not just the amount from any one customer.
If his mother has other income and files a tax return, she will have to pay tax on any money you pay her for having your lawn mowed, even if it's less than $600.
You should get the teenager's Social Security number, and issue a 1099-NEC if you end up paying him $600 or more. Don't play games with the IRS. Just follow the law and let the chips fall where they may.
