Before I start, note that I am not a tax professional, and this comes from my personal experience working in 529 administration. You should consult a tax professional in your state to get advice specific to both your state and tax situation.
It shouldn't matter who you cut the check to, but you might avoid some tax headaches if you cut it directly to your son. Withdrawals to the account owner may receive additional scrutiny by the IRS, and cause headaches in the event of an audit, or generate additional tax forms, but it sounds like this isn't really a consideration. If he receives any financial aid it can also avoid certain issues that may occur when the school receives direct payments from a 529 plan, because they can mistakenly attribute it to scholarships or grants received, impacting his qualifications for financial aid.
If he doesn't receive any financial aid, there shouldn't be any issue either way.
It would depend on to whom you made the distribution. If the distribution is made to the beneficiary or the school, and the beneficiary is not a dependent, it would be reported on their tax return, not yours.
This shouldn't matter; generally it makes more sense for the original owner to keep the account just because they retain control, and there's always the off-chance that the beneficiary decides they really, really want that Maserati. You might laugh, but I've seen horror stories when 529 plans have changed hands, a divorce occurs, and lots of other messy family scenarios. If you're making distributions to your son or the school, you're not really going to avoid headaches by transferring ownership.
529 plan contributions are already considered completed gifts for tax purposes, and you're changing the owner to the beneficiary, so there would be no gift tax consequences. That said, some 529 plans are very conservative in their interpretation of tax law, and will include language that a transfer of ownership may be considered a nonqualified withdrawal and subject to the 10% penalty. However, it has been my experience that a change of account owner to a son or daughter is not considered a taxable event, and have never seen negative consequences from this move. If you're concerned, you could give your son a POA (power of attorney) so that he can request his own withdrawals, but I personally don't think any of this is necessary unless you're just looking to avoid the hassle of having to cut him a check on a regular basis.
Brian Boswell VP, Research & Development
This information does not constitute tax advice and is provided for informational purposes only. Please consult your tax advisor, financial advisor, local taxing authority, and/or plan provider or sponsor for more information.