Per this thread

And this article in that thread

Could one use strategy 2 (Roth IRA escape hatch method) to defer taxable SE earnings for use down the road (at least 5 years) then take a taxable distribution from the Roth IRA?

Example: my dad is a farmer, farming has ebbs and flows depending on the weather, pests, grain markets etc. 4 years ago my dad made over $300k, 2 years ago he burned through a $180k inheritance just to stay afloat, and last year the large success of his other business is all that kept him from bankruptcy. He's hoping for a good year this year to dig back out of the hole. Considering that he paid a VERY large amount of income taxes 4 years ago and practically nothing the last 2 years he is looking for ways to better "even out" the ebbs and flows. Could he make tax-deferred SE 401k contributions on good years (storing away surplus), then rollover that 401k to a Roth IRA (paying taxes on it) in a bad year, let it simmer the 5 year mandate then withdraw the contribution amount from his Roth IRA?

Negatives that I'm aware of: have to wait 5 years from the time you roll it over before tapping into it, have to be cautious of contribution limits, locking away money that he may need access to in the short-term. Any others?

Benefits (other than the obvious): he's never been much for contributing to a 401k or IRA, by doing this he will build a small Roth IRA (can't withdraw the earnings).

I wasn't aware of that loophole until I just read that article; I want to make sure there aren't any unforeseen catch-22's before I inform him of this option.