My wife and I each have older traditional “deductible” IRA’s and newer non-deductible IRA’s where we made contributions for about the last 5 years or so. The balances are 90% in deductible IRA’s, and 10% in non deductible IRA’s. I also have a Keogh Plan and she has a self directed 401 K plan. Both my Keogh plan and her 401 K will accept rollover money from the deductible IRA’s. If we do a direct trustee to trustee roll over of the deductible IRA’s to these plans, that will leave each of us with only the newer non-deductible IRA’s, which we would then convert to Roth IRA’s. Since these are newer and haven’t appreciated much, the difference between our basis and the market value is not substantial and paying the tax on the gain wouldn’t be a problem. Does this plan get us safely around the IRS pro-rata rules to determine the tax on a Roth conversion? What other pitfalls should we look to avoid? I look forward to your answer.