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Peter agrees with the instructor I had this weekend. He emphasized that you should have a separate rollover account for each Roth "conversion" because if you did one this year and one next year, if they were combined then the five year period starts over.

Well, your instructor was wrong about the necessity to maintain separate accounts. From IRS Pub 590, with the appropriate part bolded:

Distributions of conversion contributions within 5-year period. If, within the 5-year period starting with the first day of your tax year in which you convert an amount from a traditional IRA to a Roth IRA, you take a distribution from a Roth IRA, you may have to pay the 10% additional tax on early distributions. You generally must pay the 10% additional tax on any amount attributable to the part of the amount converted (the conversion contribution) that you had to include in income. A separate 5-year period applies to each conversion. See Ordering Rules for Distributions, later, to determine the amount, if any, of the distribution that is attributable to the part of the conversion contribution that you had to include in income.

No need to maintain separate accounts - just a need to maintain records of the amounts converted each year.

AJ
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