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URL:  https://boards.fool.com/if-you39re-worried-about-the-difference-in-34231163.aspx

Subject:  Re: IRA to ROTH IRA Conversions Date:  6/17/2019  8:38 AM
Author:  YewGuise Number:  129378 of 130714

If you're worried about the difference in taxes, you could do a form of dollar cost averaging. Say you have 1200 shares of a stock that you want to convert. Just convert 100 shares on, say, the 10th trading day of every month, whether the stock has gone up, down or sideways. You will convert 1200 shares during the year, at 12 different price points. That should be enough price points that you will have participated in most of the up/down performance during the year.

I did something like this. Then I got a notice from Vanguard that I was close to dropping below the $50k required minimum for the (Admiral mutual) fund where I'd been keeping all my Traditional IRA money. So, being the "keep it simple" sort, I just converted the remaining balance.

Hindsight will tell whether the timing was good or not, if I care to look back, which I probably won't.
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