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Ok-Air7686 t1_iz4g4i6 wrote

You can hire the neighbors son as a contractor. He will essentially be a one man landscape company. You should ask for his tax ID number which is most likely just his SSN unless he sets up a business. Once your payments to him exceed $600 in a calendar year you will be required to issue a 1099 to him and report the payments to the government.

I work for a nonprofit in MA and we require all vendors working on our property to provide proof of liability insurance. This is especially important if he will be operating landscape and snow removal equipment on your property.

Ideally he should establish himself as a landscape company for both tax and liability reasons.

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