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Thank you for your prompt and excellent reply.

To clarify:
My IRA custodian holds my tax deferred IRA funds in multiple accounts. The number and proportion of these accounts can be easily adjusted so the accounting of conversion and recharacterization funds can be appropriately accomplished.

Also to clarify the objectives of #2.
We have determined that $10,000 (hypothetical) is the most additional "income from the conversion" that we can incur without moving into the next higher tax bracket (which would unjustifiably diminish the Roth investment). So the objective is to maximize the tax free financial gains of $10,000 invested in a Roth.
In the spirit of a contest, we would each, independently, convert (from our own tax deferred IRAs), $10,000 to separate Roths (creating a $10,000 "hisRoth" and a $10,000 "herRoth"). At the end of the year the Roth conversion (hisRoth or herRoth) producing the higher gains would be declared the winner and would be preserved. The underperforming Roth conversion would be banished to the land of tax deferred IRAs via a recharacterization. "We" collectively benefit by choosing a winner from two choices rather than just one.
As to the "administrative headache", I have never had the pleasure of recharacterizing a Roth but I assume it gets easier with experience.

Comments appreciated.

Thanks again, azBillRet
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