You're right, 1099-MISC is often confusing. I don't know why his employer issued a 1099-MISC for this work if he has always been a W-2 employee. It's possible that it's a mistake. But if the employer won't correct it, you can report it in TurboTax by following the screens for the 1099-MISC and indicate that it should have been reported on a W-2. Or you can indicate that this is not for work like your regular job, that it didn't involve an attempt to earn money, and that he only received it in 2018 (not prior years). That way he won't pay Self-Employment tax on the $772.00. The IRS can consider you to be self-employed whether or not you have an actual business if you've earned money in a relationship that is not employer-employee.
However, TurboTax Free Online doesn't handle 1099-MISC, and Deluxe Online is the next level up that handles this type of situation.
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