1. No, he would not need to file if he only had W-2 income and that was less than 1,000. (if he had investment income as well, that number could change)
2. No, Roth contributions are not reported on a tax return unless the contribution was more than the allowed amount. The contribution he made to his Roth account could not have been more than his earned income. Scholarship income can count towards Roth (and traditional) IRA contributions.
3. Yes, TurboTax can keep a running balance of your basis in Roth accounts if you enter that information.
No, contributions do not need to be reported n your tax return unless the contribution is over the limit and a penalty applies.
HERE is a TurboTax link about the advantage of reporting Roth contributions. It could trigger a "saver's credit" for the taxpayer.
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