The question can be split into two parts:
1. Best time during a given year
2. Best year
1. In theory, the best time within a year to convert is when your T-IRA portfolio is at its nadir. Which is great if you can see into the future.
Pragmatically, waiting until there's a market correction (
10% dip or more) can leave you converting at a higher value than converting now. If the market rises
15% while you're waiting and then drops
10% (to
103.5% of your starting value), what's the point? Or if you're planning on converting a bit each year, you can easily wind up stuck at the end of the year with a higher market still waiting for that correction.
If you're trying to keep MAGI under a certain "cliff" threshold (e.g. for ACA subsidies or to avoid IRMAA) then you should likely be conservative and top off your conversion near year end once you have a better handle on MAGI YTD. If your concern is about edging into another tax bracket, it's not a big deal if you wind up a few dollars over or under, so don't wait until year end for that reason.
2. If you're converting and paying taxes with non-IRA money, sooner can be better than later even if your expected tax rates in the future will be
a little higher. That's because you're effectively adding money to your IRA by prepaying your taxes. (A dollar in a Roth is worth more than a dollar in a T-IRA.)
OTOH, many states give tax breaks for retirement income (including Roth conversions) once one reaches a certain age. So it can be advantageous to wait until then. You might convert between the time you reach that age and the time you retire and actually start drawing money from your T-IRA and/or pension (and possibly using up that tax break).
Several states give
some sort of help on Medicare Part D prescriptions, where your income needs to be low enough to qualify. Doing Roth conversions earlier (even at somewhat higher tax rates) may help qualify for these or other income-related programs.
The largest such program is
EPIC in NYS. Its income cutoff is decidedly middle class: $75K single, $
100K married.
The rule of thumb short answer is the sooner the better (both within year and across years); just don't do too much in a single year and keep various income thresholds in mind. And if you're thinking of making charitable contributions, keep some money in the T-IRA so you have it available for QCDs.