Dan Caplinger

If you convert at a time when the market was high and then the market drops, you still have to pay the tax on the higher amount.

So that can be a disappointment.

Secondly, if your tax rate ends up being lower in retirement than what you paid at the time of the conversion, then it might well have been a smarter move just to kind of leave that money in the traditional IRA in the first place.

Again, though, there are those offsetting benefits.

So it's not such a clear-cut answer even in that situation.

Thirdly, bro, and you touched on this, the fact that you can touch those Roth IRA contributions, having that easier access can be a temptation.

Sometimes it leads people to take money out for reasons other than retirement.

That hurts their retirement prospects down the road.

And then lastly, when you do that Roth conversion, you have to pay attention.

It can be a big taxable event.

And again, those second order impacts, the converted amount can be what kicks you up into additional Medicare payments, into more taxation on Social Security as well, depending on when the timing of the conversion is.

All right, Dan, do you have any final thoughts or recommendations?

Last thing I'd say is just when you're considering a Roth conversion, don't look at it as an all or nothing proposition.

You can do it a little bit at a time.

And a lot of the time that is the smartest strategy because you can take advantage of low tax brackets without paying tax in the higher tax brackets.

Little by little, sometimes is the best way to get these things done.

It's something to pay attention to in those years before the requirement or distributions kick in, but after you have decided to retire, sometimes that's the best time to consider a Roth conversion.

It's incredibly difficult.

It makes things very difficult as a long-term investor.

The reason for that is that you suddenly run into all these situations you wouldn't normally run into.