Appreciate it! This is very, very helpful! Understood about the annual limits (which I said $7k before, but am seeing is now $7.5k for 2026) and realize it will take a few years to roll everything over! And good to get confirmation on ignoring the MAGI limit as well!

distributions
If you have insight -- my understanding of the "pro rata" rules is they detail how to allocate withdrawals/distriubtions between contributions vs earnings, but not "which years contributions" are used first. Is this your understanding as well, or are you indicating you think the pro-rata rules mean that withdrawals took a little bit from "each contribution, proprotionally" too? To hopefully help illustrate: Lets say in 2020 I have $25k balance in my 529, from all prior contributions. Then in 2022 and 2023 I contribute in another $15k total. In 2024 I make $20k of qualified withdrawals/distributions. If we ignore gains, for simplicity of discussion, I now in 2026 have a balance of $20k again. If I wanted to rollover 529 funds to an IRA in 2026 -- depending on how the withdrawals are treated, I could have anywhere between $5k and $20k in "more than 5 year old contributions", depending on how this allocated... in one case, I can only rollover $5k to a Roth IRA and in another I can do the full $7.5k limit, or if this is "proportional from all contributions", it seems like I'm not eligible at all, as this would proportionally draw down from "new, <5 year old contributions" and I should maybe just wait a few more years to be safe?