Based on this article from Fidelity, it appears that the tax basis for a Roth conversion is the net value of the retirement account at the time of the conversion.
As such, let's say I have a traditional IRA worth $10k prior to a market downturn, for which my tax basis would have been $7k. If I had invested in a Roth account initially, I would have paid taxes on the $7k I invested.
Now let's say the market declines, and my portfolio hits a value of $5k (quite possible with my risk tolerance). If I convert at this stage, I would only pay taxes on $5k. Sure, in a 25% bracket that is only $500, so nothing terribly outstanding, but the question scales, and I just picked convenient numbers.
Taking advantage of this doesn't require predicting a market downturn, which is another topic entirely. Instead, it only requires that we expect that market downturns will occur.
Because of increased regulations in the US recently, it appears that we are seeing less large scale volatility. While markets still rise and fall, some protections ensure that events like the late '90s tech bubble or the '08 housing crisis don't have the same impact on the markets.
So, I wonder whether it's better or not to wait for a possible market downturn to perform a Roth conversion.