No, you do not have to prepare a 1099-MISC for HOA dues unless it was for a rental property and you paid over $600.
As long as you have proof of the payments, you can justify your deductions. Just make sure to save your proof.
I've pasted a link to the requirements to issue a 1099-MISC for your use below.
In general, you do not have to prepare a 1099 for any corporate recipient (C or S Corps). There are some exceptions. But your question specifically referenced HOA dues...these payments are not for services and they are not payments of rent, so no 1099-MISC would be necessary.
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