If you convert to a Roth IRA in 1999, the Roth IRA regulations permit you to recharacterize back to a traditional IRA and then convert again once this year.

In one of Barry Picker's articles at he suggests that if you convert into several Roth IRAs and one of them drops in value, you could recharacterize that one Roth IRa and then reconvert it. (I suppose the extreme case would be to put each separate security into a separate Roth IRA.)

This seems consistent with everything else involving IRAs (for example, if you have several IRAs, you can calculate substantially equal periodic payments separately for one IRA for purposes of avoiding the penalty for pre-59 1/2 distributions). But I would appreciate it if others would confirm that the above is their understanding as well. I have a client who set up several Roth IRAs so that he could leave each one in trust for a different beneficiary and be assured that he would get the benefit of the different life expectancies (which he might have gotten anyway, but there is some question as to that issue).

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Bruce Steiner, attorney
(212) 986-6000 (NY office)
(201) 862-1080 (NJ office)
also admitted in FL