Why do you think it’s a good time to make the conversion when you retire? Just for grins, say you have $5M in 401k/ira and you are 65 years old. Plus, say right now you are in the $0 tax bracket. Now, you want to say you want to convert $1M a year to a Roth for the next 5 years, do you know what tax bracket you will be in each year? You would be in the max tax bracket, your Medicare payments will jump by 5x or more every year you do this plus 1 year, your social security will be taxed at 85%, on and on. So you sell $1M of your 401k/ira and you get to take a little over $550,000 and invest it. Do this for 5 years, you will end up with $2.5M-$3M.
Now I keep what I have and it compounds by 8-10% each year on average, my $5M will grow to $7.5M-$8M in 5 years (3x more than what you would have with the conversion), let them tax the hell out of me in 5 years each year, but I guarantee you, I will not be anywhere near the top tax bracket and the more money I have in my 401k/ira accounts, the more it will grow, and my growth per year will pay any taxes that will be levied to me.
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