This is a really fun idea. I like the rating system, simple and easy to implement. Borrowing the flashback from Blades on the Dark is a nice inclusion. And the guild itself suggests various other Robin Hood style adventures. Nice.
Thanks! The flashback mechanic was actually inspired by Honey Heist. I've never played Blades in the Dark, but I'll have to check it out!
I think you'll love it. This sort of heist scenario is a big part of it, and the mechanics cleverly support a set up where everyone is a rogue.