1) Yes, he needs to file.
2) Please see Tax Expert TomK's advice here/below to enter this properly:
There will be a few steps to follow to report your stipend correctly because of the form 1099-MISC.
If box 7 reports the stipend, you would have to report it as self-employed income, then enter the same amount as your "business" expense. This will ensure that form 1099-MISC is reported for matching purposes, but the amount is not taxable as self-employment income.
Go to:
1. Federal Taxes
2. Wages and Income
3. Self-Employment, Select Income and Expenses - follow the interview questions; you would report the stipend as if you own a business; once general questions are answered, you would enter the stipend as an expense (you can create your own description). The end result: form 1099-MISC is reported, but the income is not self-employment income--because it shouldn’t be.
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