I have been contributing to a 529 plan since my was born more than 15 years ago. I am the account owner and he is the sole beneficiary in this 529 plan. So, this 529 plan has one account owner (which is myself) and one beneficiary (my son). This is the way it was since the inception of this account. I have been paying for his college expenses out of the funds from this 529 account. Now that he is almost done with his college, I will have $50K left in this account after he finishes his college. Now, I recently learned about the 529 plan to roth ira conversation and if I can take advantage of this conversion with me as the beneficiary. Here is what I am thinking.

1. I am planning to change the number of beneficiaries on this account from single beneficiary (i.e. my son) to 2 beneficiaries.
2. In other words, this 529 account will now have 2 beneficiaries, one is my son and another is myself.
3. Let’s say that I would still keep $10K for my son as the beneficiary and $40K for myself as the beneficiary.
4. I am thinking that this would be same 529 account because I am still the account owner. (If this is not considered the same 529 account when having multiple beneficiaries, please let me know).

Here are my questions?

1. I am wondering if I can transfer any of the $40K (for which I will now be the new beneficiary) to my own personal roth ira account? Or does the 15-year rule preclude me from doing this for my own benefit because I was not one of the original beneficiaries 15-years ago on this account?
2. If I can do this above, can I do the same with another 529 account for my second son (with similar situation)?
3. Are there any caveats to doing both (1) and (2)?

Thanks

Rag/..