In both ESPlanner and MaxiFi, the Roth conversion strategies are still "manual" in a sense. The software is not going to iterate 50 or 100 or more times and test out different conversion amounts in different time periods etc. and reveal an answer like: convert this much in these years. Instead, you must enter an amount you want to convert as a special withdrawal from your 401K (causing you to incur the tax) and then indicate a contribution to the Roth for that same amount in the same year and then compare the discretionary spending of the two cases.

I don't know of any rule of thumb to guide this decision about amount or timing. It's possible that this conversion can make a significant difference, especially with big sums, but I've also seen it more often I think only increase discretionary spending by a few hundred dollars a year over the lifetime. May still be worth doing.

There seems to be a lot out there on the web with regard to withdraw strategies--bucket strategy and this or that. I probably think too simply about it but wouldn't one just sell what is high and hang on to what has dipped? And isn't it true that there's no way to know what will be high or low a year from now, 10 years from now, 30 years? Thus, I'm sometimes confused by a customer that asks (not you or what you are asking here) if our software addresses withdraw strategies.

Anyway, the Roth conversion is worth looking at.

Chris is a super saver. :)

Check out www.i-orp.com, which is useful for modeling Roth IRA conversions. It has been updated to the new Tax brackets. Be sure to read the docs for input fields and interpreting the report output.