Should I change my regular IRA to a Roth?

Tonight is DEC. 29. You have two---actually one and a half (business) days to decide for this year. There is a very special rule you need to decide by Friday. So, run to the phone, and call Vanguard or other funds that can steer you straight about this one time rule.

Basically, you can with draw/convert from the (untaxed) regular IRA into a ROTH (which is post taxed dollars). You then can spread the tax liability of your withdrawal over two years. After that, the rule expires. Now, as has been written by others, you have until age 70 1/2 to take out the money from the reg. IRA. After that, there is a formula forcing you under penalty to take it out of the REG IRA. And you might just make it (tax liability-wise) with little or no tax depending what and how much, and when you do it.. But, I can't tell you with out running ALL your income numbers, including SSI, Pension, 401k, etc.

Yes, you missed a nice tax window, but now IT IS WHAT IT IS. So, please start ASAP, and talk to Vanguard specialists and Turbo tax preview, or just get the program, or talk to a provider.

The main considerations when rolling over a regular IRA to a Roth IRA is that the taxes that you haven't paid on the funds in your IRA will come due during the year of the conversion, the Roth IRA doesn't have the same distribution rules (i.e. you don't have to distribute your entire account by age 70 1/2), and the potential tax benefits of having the funds in a Roth IRA be distributed tax free.

If you're going to hold onto the Roth IRA past age 70 1/2 you could see some benefit from the conversion but, in my opinion, the sooner you're going to need that money the less the conversion makes sense. I'd be sure to consult a tax advisor given how close you are to social security though - you don't want anything you do with your IRA to affect that...

So, you have had no income for 2010, zip,nada.

Your first $9350 (single, adult) is taxed at 0%, so I'd certainly have been rolling that much per year over to a Roth.

I wouldn't - in those circumstances. I'd just keep my IRA distributions low so there's minimum tax bite. Converting it now in one lump sum doesn't make sense.