Hey All - I was reminded of the work I did on this for my own understanding about a year ago. Please check my method and understanding. Note this is all based on current law and I cannot predict the future changes in that arena.
OK. My goal was to compare what you can do with a dollar, and what place it would have the best impact. The 4 'vehicles' I compared were: Invest it in a 401k/403b/Traditional IRA, Invest in a Roth account, use the dollar to pay income taxes to convert existing 401k to Roth, and then just a regular investment account. I tried to normalize everything assuming you have access to the same funds/fees/ return rate, etc in all vehicles. I also normalized by saying the investment was an 'after tax dollar' or essentially a dollar from your paycheck. If you invested in the 401k, it would be inflated by the tax savings, so the $1 invested would actually be the pre-tax amount you would be able to invest (more than a dollar). Similarly the roth conversion isn't actually investing anything, it's taking the dollar to pay the required tax to convert pre-tax money to Roth.
Looks like this (you can change the variables on the right and see the results on the bottom of the left):
What we learn is that if your tax rate is the same at withdraw as it is when you deposit, there are differences in total tax paid, but no difference to your bottom line. Perhaps obviously, if you pay more in taxes now than when you withdraw, the 401k is best. And if you pay more taxes at withdraw, then conversion is best.
Also, perhaps less intuitively, if you need to withdraw before age 60 and therefore pay a penalty, the Roth investment account wins (unless maybe you have a large difference in current and future tax rates):
So now that we see the results, let's talk about the methodology (because this is what I want to double check).
401k: If you invest a post tax dollar here, you actually get to invest the pre-tax dollar (assuming you haven't yet hit the annual limit), so I take the dollar and mark it up based on the current tax rate. Money grows at standard growth rate for the number of years between age withdrawn and deposited, and taxes are calculated on the withdrawn tax rate and the entire pre-tax amount. If the age withdrawn is less than 60 there is also a 10% penalty assessed on the gains only.
Roth: If you invest the dollar here, the pre-tax account and post-tax account grown individually. Taxes on withdraw are only calculated on the pre-tax amount. If early withdraw penalty applies, it applies only to the gains.
Convert to Roth: This one is a bit tricky. This is saying you use the $1 to pay taxes on converting existing pre-tax to post-tax (and assuming you have enough pre-tax to convert). So the $1 is not invested. Rather I use the tax rate to figure out how to split the pre-tax amount into pre and post tax accounts. From there i follow the Roth methodology.
Standard: Should be simple. The pre-tax account stays, and there is no post tax account, but there is a separate 'pre-capital-gains' account. You'd pay withdraw tax rate on the pre-tax amount and you'd pay capital gains rate on the gains in the 'pre-capital-gains' account. The early withdraw penalty only hits the pre-tax balance only.
Question: Does the early withdraw penalty apply 'before' the taxes are calculated or 'after'? ie are you taxed on the amount before penalty or after?
In conclusion, this isn't the whole story, as it doesn't even start to get into the RMD discussion. It also leaves out investment vehicles like your primary residence (essentially a roth because it is post-tax money that is not subject to capital gains tax). But what we do see is that unless there is a large difference between the tax rate you pay now and the rate you pay later, all methods work out pretty similarly for you.
tl;dr - invest your saved money somehow.