When I get to the page asking "Tell Us The Value of your Roth IRA", is it asking for the value of solely my 2019 IRA or my 2019 PLUS all previous years' value?

The subtitle says "Enter the value of your Roth IRAs on December 31, 2019. Note: Include any contributions made after December 31, 2019 that were designated for 2019."

posted

It's asking for the sum of the values on December 31, 2019 of all of the Roth IRAs of which you are the participant, plus any amounts contributed to those accounts in 2020 for 2019. (Do not include the values of any Roth accounts in employer-provided qualified retirement plans; those are not Roth IRAs.)