When rolling over ESOP distributions to an IRA, can a portion of the IRA be allocated to a Section 529 plan (NY) without any taxes and/or penalties being levied? If so, what basis is picked up for transfer to the 529 plan?

529 plans are state plans that allow individuals to put after tax amounts into a fund to pay for college eduction in a particular state. The funds are not subject to the federal gift tax. But the contributions are made on an after tax basis of as much as $11,000 a year. The only advantage is a state tax deduction. NY's 529 plan is managed by TIAA-CREF. who you can call for further information.

. . . and additional tax advantages are tax-free growth and tax-free distributions for qualified educational expenses. The answer is "no", you can't make a tax-free transfer from an IRA to a section 529 plan.