I’m in my mid fifties and planning to do Roth conversions as follows
* Do Roth Conversions annually to fill up the 15% bracket till I take Soc Sec at 70
* Multiple conversions would be done in Jan each year separated into multiple accounts by asset class
* Total conversion amount each Jan would exceed 15% bracket need substantially
* In November each year I’d keep the winner(s) and re characterize the rest back to the IRA
* In November if some accounts have risen in value by 10% in the year, then I’d convert into the 25% bracket.

I understand I can have much longer to recharacterize but I want to keep things a bit simpler

Does this plan sound reasonable? Any big holes?

Thanks,
Ray