My main issue of late is that after my legal name change, my bank reissued my debit card with the same number. It's nice that I didn't have to go through the hassle of changing it with everyone who has it on file, but what happens sometimes is something like this:
Cashier: "I'm sorry, we have this card number under a different name."
Me: "Is that a problem?"
Cashier: "Well, it looks like you may be committing some kind of fraud."
Me: "No, there's no fraud going on here. This is my card."
Cashier: "What's your address and phone number then?"
Me: "<home address and phone number>"
Cashier: "That's what we have, but the name we have is Gregory <lastname>. Do you know him?"
Me: "That was me before I transitioned."
Cashier: (choose one) "Holy crap!"/"Umm, OK. Not what I expected."/"WTF?"/"Oh, my <distant family member> is trans* too."/*blank stare*