You could estimate the tax efficiency of your taxable investments to figure this out. You could do this one of two (or many) ways.
First, you could estimate your future effective tax rate for your taxable investments. I do this by determining the amount of tax I've paid over the years on my investments at my marginal rates (with the addition of estimated taxes due on unrealized capital gains) and dividing that by my investment gains (including unrealized gains). This approach is better than just using capital gains rates each year because it gives credit to some extent for trading strategies that reduce taxes and also it reflects actual durations that I hold assets. If you just used capital gains rates, then you would have to make assumptions about how often you sell assets (you flip everything every year, you hold everything until the end, or something in between), and how much of your return is dividends. This approach is time-invariant, but suffers from not taking into account the amount of earnings that your tax payments could have earned had they been invested instead of being paid to Uncle Sugar.
Alternatively, you could estimate the effect of taxes on your returns. First, estimate the returns on your investments before taxes (I use the XIRR function in Excel for this - be sure to include flows for selling your entire account). Then estimate the returns while including the cash flows from taxes paid (again I use the XIRR function in Excel, but I include cash flows for taxes this time). Dividing one by the other will give your tax efficiency over the period. The advantage here is that you include the time value of tax payments, but the result you're looking for is no longer time-invariant, you would need to look to see if there is a break-even point within your investing time horizon where the taxable account becomes less effective than the taxable IRA.
Of course, these are just estimates, tax rates will change in the future, favorable capital gains tax treatment may go away, and your investment style will fluctuate. And of course, you may want to use a taxable IRA just so that you can roll it into a Roth in 2010. But this will give you a basis for playing around with the numbers. In my case, I've decided that taxable IRAs are not for me, I use taxable accounts instead, given the tax efficiencies that I have so far achieved.
-Will