Retirement tax questions

1099-R does not list FUNDS:

you must be looking at a consolidated 1099-B.

Let's say you have dividends  (1099-DIV) from four Vanguard funds.

 

If you have a regular old style Vanguard account you must itemize the fund dividends.

If you have the new Vanguard Brokerage type of account, you can enter

one line for "Vanguard Brokerage" and enter the total of all dividends.