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I hired a contractor to do some stucco repair as part of my installing solar on my house.

Is there any documentation I need other than the canceled check? Do I need to get a ITIN/SSN from him? (And if I can't get one, then what?)

It sounds like this is work for your personal residence. Assuming that is true, then you do not need his SSN as you are not issuing a 1099 since it is for a personal residence.

If you are looking for documentation to take the tax write-off on the solar, then you need a receipt from him for the work.

Since he cashed my check at my bank, I suspect he's not a documented worker - but it's possible he just doesn't like banks or has some other reason.

Actually, that's a pretty broad assumption. My DH is a General Contractor, and sometimes I deposit checks from his customer, and sometimes he cashes them. In all cases, I record the transaction so that I can report it as income, but that has nothing to do with how he treats the check.

In cases where he cashes the check, it is typically to make sure that the check is actually good. There are lots of reasons, though, to cash the check vs. depositing it. I know that when I pay his subs, more often than not they cash the check at my bank, but that doesn't matter to me. I still track it and issue the 1099 as needed.
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