Should I do Roth IRA conversions after a market crash?
I have too much money in my traditional IRA and not enough money in my Roth IRA. Both accounts use VTSAX. I have no intention of touching it any time soon. Since it seems that markets tend to drop quickly (& noisily) and come back slowly (& quietly), why don't I wait until the next market crash, and THEN convert a lot from traditional to Roth?
I presume that after the market comes back from a crash its recovered (Roth) gains will be tax free. And my loss from selling (traditional) may generate a capital gains loss (probably not). I'll certainly be paying less taxes on each share of post-crash VTSAX.
But I'm just selling VTSAX shares in this account to buy them in another. Can this be construed to be a wash sale by IRS? (It's really just a Roth conversion, sir.)
Since I've had these accounts for a long time, I think my basis is very low. So that I may have some capital gains even after a major correction. Would this would moot the wash sale rule?
Is this a stupid strategy? Are there any gotchas I haven't foreseen?