The basic rule is that you issue a 1099 to anyone who is not an incorporated business. All sole proprietors should get a 1099 from you. If this was an incorporated business that issued you a bill then there is no need for a 1099.
What I will tell you is that if you're in doubt then get a W9 from them and issue the 1099. Why deal with the potential headache?
@GCKirt
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