Below are the answers to your questions:
1. If your friend can't be claimed as a dependent by another US taxpayer, he can file as a nondependent.
2. As a F1 visa holder who's been in the US for more than 5 years, he's considered a resident alien if he passes the Substantial Presence Test.
As a resident alien, he files form 1040. He can use TurboTax Online or CD/Download.
3. He is an alien and isn't eligible for education credits such as the American Opportunity Tax Credit (AOTC) or The Lifetime Learning Credit (LLC).
4. He has to report his form W-2 and all other income if applicable. He can't claim education expenses.
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