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I built a new house in 2016. Do I need to send every contractor/sub contractor that worked on the house a 1099?
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Assuming this house was is your residence the answer is "No".
If you are "in the business" of building houses for sale then the answer is "Yes" if the contractor/sub contractor is a sole proprietor/independent contractor, (i.e., not a corporation (including a limited liability company (LLC) that is treated as a C or S corporation) and you paid that person more than $600.
If you need to prepare 1099-MISC then you should read the instructions: https://www.irs.gov/pub/irs-pdf/i1099msc.pdf
Tom Young
