That makes no sense to me. There are thousands of early retirees who are similarly situated to us... living off of savings with reinforcements of pensions and SS coming later... that are in low marginal tax rates now but will be in higher tax brackets once pensions and SS start... for who Roth conversions are really compelling.
He's a pretty smart guy... why would he have not thought of such situations?
He says:
It makes little sense, in my opinion, for most near-retirees to assume their tax rates will rise.
That is likely true, if you haven't yet retired, your tax bracket is probably higher now that later.
But then he does on to talk about his own situation when he did retire early. In which case I agree fully with pb4's quote above.
Then again, maybe he's making as much money from blogging as he was before, though some might not call this retirement.
This part turned me off pretty quickly:
But first, be forewarned that I have a strong distaste for adding complexity and paperwork to my life just to save a few bucks. Especially if that payoff involves parting with my money sooner than later, or requires predicting the future accurately.
The author seems to scoff at increasing net worth only a few percent when they are older. That sounds like a great gain to me, for doing nothing more than a little paperwork to do the transfer and account for it in my tax return. Does he need something to double his net worth before he'll lift a finger?
And the parting with his money now argument is flawed too. You CANNOT access tax deferred money until you pay a tax on it. It is not all yours. Paying now vs. later is all baked into the conversion analysis.
You have to predict the future accurately? No, you just want to make a calculated estimate, really, just a direction of your tax rates. Given the national debt, do you think tax brackets in the future will be higher or the same? Will adding social security and RMDs put you in a higher bracket, or at least the same? If you're married, and one of you dies, will filing single for close to the same amount of taxable income put you in a higher or same bracket?
Note that even if you answer "same" to all questions, a Roth conversion won't lose you money. If you answer "higher", you'll do better. The only time you lose is if you answer "lower" to one or more of those questions, without balanced by a "higher" to another question. It doesn't require accuracy, just an idea of your personal tax situation with respect to questions like this.
The difficulty might come in trying to decide whether to go to the top of the 12%, 22%, 24%, or higher bracket with your conversion. Just because that's a harder question to answer doesn't mean you should do nothing. If you're pretty sure that conversions are a good idea, but not sure how much, you could be conservative and convert to the top of 12% or whatever bracket you are pretty certain to be worthwhile.