Oh man, medallion signature guarantees. My wife has an old IRA in Schwab from before we were married, and I wanted to combine it with her Vanguard IRA for simplicity. Turns out either Schwab or Vanguard (maybe both) wanted a medallion signature guarantee to perform the rollover. I have a Wells Fargo checking account so I asked at my neighborhood branch if they could do that for me, and they said yes, but only one guy can do it, and he's only there a couple days a week, and I'd have to make an appointment, and because it's my wife's account I'd need to bring her to the appointment (which in turn requires finding a time that both of us and the bank guy are available and also we have child care). It was on my to-do list for a while, and then the pandemic hit, and the result is that account is still sitting there at Schwab. It's crazy because with our online account login we could easily sell all the shares and liquidate the account and transfer the whole balance to our checking account, but if we want to transfer it to another IRA they want this special proof that we are who we say we are. I'm sure someday we'll get that done, but it's enough hassle that it hasn't really seemed worthwhile to get it done yet. Schwab's index funds are just fine. It's annoying to have this one account with like 1% of our net worth in it, being held by a completely separate company from the rest of our assets, but it's also annoying to fill out the paperwork to combine everything, so status quo bias wins the day so far.
I guess if I were in your shoes I'd try to just sell the shares pretty early on in FIRE without bringing up the name thing. If you run into any problems going through the company's normal process you can pursue the medallion guarantee thing then, but why bother if you can get your money some other way?
