I think I have a pretty good understanding of the Roth IRA ladder concepts, but I'm not sure on the execution details. I'm looking for guidance from people who have actually started to use their Roth IRA ladders in FIRE. Some quick details about my situation:
I am FIREd and have >5 (about 7-8) years of expenses in after tax accounts. My last day of work was in April of 2019. My income from the first 1/3 of 2019 and savings carried me through 2019. Starting in 2020, this year, I will have zero income from employment for (hopefully) the rest of my life. My plan is to use my savings and post-tax investments to pay my bills for the next 5 years, including 2020. To generate income to spend in 5 years and to generate income to get me above the Medicaid thresholds and into the ACA bands, I plan to transfer money (let's say $25k for example) from my 401(k) with Fidelity into a Roth IRA with Vanguard. This will be the first rung in my Roth IRA ladder. I will continue this each year moving forward. I think I understand the process conceptually pretty well, but I don't know how to actually do it.
My question is this - how do I actually execute this? Do I do some sort of online transfer? Do I call Vanguard? Do I call Fidelity? If I call what specific verbiage do I need to use to get them to understand what I want to happen so the transfer is properly executed? Would this be substantially easier if everything was with Vanguard? The fees with Fidelity are extremely low and I'm happy with the investment options so I'm not looking to move everything to Vanguard, but I could if it would help make this easier.
Any help would be greatly appreciated.