Thing with the bar owner feels weird because Simon spends all of C1 being all dark batman ends justify the means but then takes a swerve to whiteknighthoodville for the rest of the game. He does still do morally quesionable things but none really for mere power or advacement, and even when he does toe the line there's like 50 characters tripping over eachother to reassure him of his goodness. Just kind of an OOC moment looking back, same for selling out the succubus or mindbreaking that other girl, and it's kind of a shame too since i feel the game suffers from corruption being such a big theme yet Simon being so inhumanely incorruptible. But what can you do.
The game mellows out in the later parts. I think Simon was always intended to be presented as incorruptible, but early on the game had more scenarios where "darker" alternatives could still be rationalized as the "lesser evil" given the limited number of choices and relative powerlessness of the protagonist in face of the challenges they would have to face.
But to be fair, the game at least adresses this in a conversation later in the story. Ruthlessness is something that makes more sense when you don't hold much power, both because ultimately you can't cause much damage in relative terms, and the opportunities to gain the power you need to accomplish your goals are much more scarce.
Once the protagonist became a powerful ruler, the dynamics change and it becomes more important to be cautious with how one wields their power, as well as the pursuit of more power not being as important as using what you already have for the greater good. After all, power was still just the means to achieve the best possible result, if you are already strong enough to achieve the best solution to most of your goals, it doesn't make sense to sacrifice them just to keep accumulating more power.
