TurboTax is asking these questions so that dividends will be taxed appropriately. Next to several of these questions are "learn more" links. If you click the links, you might find enough guidance to answer your questions.
Vanguard will likely not provide advice on how to report the dividends. If the "learn more" links do not help, you may be able to answer your questions with a little research into the funds themselves. There should be a fund name that you can search online for further information. You also may have received some literature with the 1099-DIV itself that can shed some light on these questions.
@rvmeush
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