Can I simply take a withdrawal from my 529 account, cash the check and then make a check payable to my Roth IRA custodian?
No, indirect rollovers are not permitted. For the rollover to be tax-free, you must request a direct trustee-to-trustee transfer; meaning that it must go directly from Embark to the Roth IRA trustee. You are not able to take possession of the funds yourself. Account owners must establish a Roth IRA account before requesting a rollover. Once the Roth IRA is established, you will need to submit the form identifying who the IRA custodian will be, and Embark will make the check payable to them.