Idk about Annie being the one to offend him. I mean, I'm sure she has. Easily. But she'd be cruel and vicious right at him particularly with the very loudly spoken words, "What? You're such a little bitch you can't just attack me and leave the rest of 'em out of it? Come on, pussy. I'm more of a man than you'll ever be, you fuckin' loser." As said, Simon's a neutral type so unless Prince pisses him off first... Simon will be good.
As for Rodeo... I do believe we discussed him and Annie will gladly take him to her bed. For a price. I have this mental image that there's an arrangement that she'll give him a discount on whatever if he manages to make her come. That's just the way she rolls. Simon is saddened by Rodeo's feelings but respects his personal space.
Annie thinks Lucky is a fucking moron. What's more independent than charging for the pleasure of her company instead of tying herself to one moron male for the rest of her life? Simon would like to meet Lucky but hasn't approached him on his own.