Today happens to be payday for me, and I was updating my spreadsheet last night (my bank reports the deposit a day early) and decided to switch my autopay around a bit. I basically have the following accounts:

Fidelity brokerage 1 - used for bills and whatnot
Fidelity brokerage 2 - emergency fund, also where deposits go
Fidelity Cash Management - personal spending (SO has their personal spending at another bank); used to be w/ credit union, but I wanted money market funds for better returns

However, I messed up, because the CMA needs to be the account hit w/ spending to do any form of overdraft (I've been handling this by keeping a month's expenses there at all times). So I started the process of switching our regular bill pays to the CMA, and apparently my new mortgage company is a giant pain because I can't access the autopay at all (no payment due, so I can't switch the next payment...). It's incredibly dumb, so I'm going to have a weird hybrid of personal money and family money for a few weeks while I sort out this nonsense. I could open a new brokerage account, but then I'd have to close it in a month and that sounds dumb.

Part of me just wants to pay off the mortgage and be done with it because I'm constantly running into stupid issues like this (i.e. if I want to change my insurance, I need to pay for it, then send the details to my mortgage company so they can pay for it going forward because they need proof of insurance). It really shouldn't be hard to switch which account pays a bill, yet here we are. But my rate is so low that it would be stupid to pay it off early, so I'm delaying until I'm FI.

Have any of you run into something stupid like that? What annoyances are you looking forward to completely eliminating once you're FI?