dmertz, Thank you for the reply. With respect to your warning about becoming subject to Net Investment tax (as well as some other things you said), I have some questions: 1. If I don't retire for five or ten years is that Medicare issue you brought up moot? 2. Aside from that Medicare issue, is staying in the 24% bracket my primary benchmark/metric? Or maybe in simpler terms, if I accomplish the goal of a Roth conversion while staying in the 24% bracket, is there any other thing I need to worry about or take care of? 3. Can I use Turbotax to prepare the simulated tax returns you mentioned, and does that just mean almost finishing a return, writing down the results, then going back and changing stuff and almost finishing it again? ... View more

fanfare, my reply is below. dmertz, I will read yours and reply seperately. I am about to turn 60. My wife is 40. She is pregnant with what will (probably) be our only child, so I will keep working as long as possible. (yes I'm going to get tired on many days, and yes I might be a knucklehead). In addition to the 700k in tax deferred Vanguard funds I have about 240k in savings stashed in a non-retirement Vanguard account. 80% of all my money is in Moneymarket funds at the moment. I'm carefully watching and reading many books about investments and Social Security and all that. Learning it enough to actually know some stuff and not just be dangerous is hard, especially when I'm still working a hard job. But one thing that seems to be getting more clear is this idea of taking advantage of low tax rates and biting the bullet and paying some of the taxes by a Roth Conversion. I was thinking about maybe doing it two or three times the way I asked you about in the first post.  ... View more