On a similar note, I still do not understand why I have to plug a USB Flash Drive into my Mac twice for it to mount.

I take modern USB-C Flash Drive, plug it into my Mac. Nothing. Take it out, plug it in again, and it mounts just fine.

Same with SD Cards.

I have no idea why this is, and I'm not sure if it's always been this way, but I can't remember a time when I didn't have to do this.