1) No, when TurboTax asked about your basis, after you entered all your Form 1099-Rs, you will enter the aggregated basis from your traditional IRA and the rollover traditional IRA. The IRS see all traditional IRA's as one account for Form 8606 (exception if you have an inherited IRA, then you need a separate Form 8606).
No, you must enter the value of all your traditional, SEP, and SIMPLE IRAs on December 31, 2024, in the retirement section. Therefore, you need to add the value of the traditional IRA and rollover IRA together. You can see them on your end of the year statement.
2) Yes, the basis in the Deduction section is the total of all cost basis of all traditional IRAs (i.e., $0 for the Rollover IRA + $XXX for the non-deductible IRA; the Roth IRA should not be included). This basis question and the retirement basis question are the same.
Note, the end year value question during the IRA contribution interview is different from the value question in the retirement section. In the IRA contribution section the value question only comes up when you have an excess contribution. TurboTax will asked on this screen to enter the value of the traditional IRA on December 31, 2024, including contribution made in 2025 for 2024. TurboTax uses this value to calculate the penalty on Form 5329.
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