Do you both have Roths now? If not, you each might want to open and fund accounts now to start the 5 yr clock on your first Roth. After you turn 59.5,
that is the only clock that matters:
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see this partial table by kawill from the fairmark.com site:
for Roth withdrawals:
OVER AGE 59.5
LESS THAN FIVE YEARS SINCE OPENING FIRST ROTH IRA
Contributions: Tax-No ;Penalty-No
Conversions: Tax-No; Penalty-No (Taxable Portion)
Conversions: Tax-No; Penalty-No (Nontaxable Portion)
Earnings: Tax-Yes ;Penalty-No
OVER AGE 59.5
FIVE YEARS OR MORE SINCE OPENING FIRST ROTH IRA
All Distributions Are Qualified
No Taxes
No Penalties
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Once you turn 59.5, there are no more 5 yr clocks on your conversions.
If your first Roth is < 5 yrs old, withdrawal of earnings will be taxed;
However, the ordering rules say that withdrawals are considered to be contributions first, then conversions, and earnings last so it is likely that reasonable withdrawals will allow the Roth to age to 5 yrs before you get to earnings at which point, all distributions are qualified.
You may want to consider delaying SS (and possibly the pension) if you can survive w/o them. That would give you a lot more space for the Roth conversions at reasonable tax rates. A common rule used is to convert
up to the top of the 15% bracket. If you file income taxes jointly w/ std deduction, that gives you 90+K of AGI space you can fill with conversions and other income.
You should try to keep the conversion tax rate no higher than what you would pay if forced to take RMDs later from the TIRAs.
Have you seen this site which claims to maximize spendable income in retirement:
http://i-orp.com/
To many, it seems to be heavy on Roth conversions.