Let's assume you contribute a certain deductible amount to your IRA on Jan/2, and invest it there. You really want the money in your IRA Roth at the end of the year, but you try to pick the best approach after the fact:
- if during the year your investments go down, you convert the investment at some point in time, and produce taxable income only for that lower value'. You get a negative income (the difference between deductible contribution and the now lower converted amount), which helps you save some taxes.
- if your investments go up, you 'change your mind' in December, and recharacterize your original contribution to Roth. The gains therefore - retroactively - happened tax-free inside the IRA Roth - great!
I don't see a reason why this would be illegal or not workable?