Robin being this skilled of a thief….dare I say he was once an assassin of sorts? Not like Graham the “Huntsman”, but Robin being like an actual hitman/thief. Along with robbing, he killed whoever he was assigned to kill.
I’d quite like that because it would mean he’s dealt closely with people like Regina before and even been on their side. It’d make me believe how he could have faith in her changing, if he had been involved in that same world but got himself out of it.
And would make sense with what Tinkerbelle once said about Regina ruining his life. Instead of Robin now being the light to Regina’s darkness…Perhaps Regina was supposed to be the light to Robin’s darkness, but because she didn’t go into the tavern, Robin succumbed further into it, forcing fate to cause a different situation which then set Robin on the right course, because then Regina would need someone to save her from the darkness in present day.
"If you go as far as you can see...you will then see enough to go even further." - Finn Balor