Great post, but I'd also like to add in that Jimmy isn't....well, he isn't normal, I guess is the best way to put it. By which, I mean he has a fundamentally different perspective on the idea of lies and truth than most people, in that he doesn't see anything wrong with lying if it gets you something. We talk about Jimmy and how his path was influenced by Chuck's hatred of him, but I think it ignores that Jimmy is pathologically wired to be a scammer.
Like, there are numerous occasions where, upon being forced to be honest with people, he seems genuinely baffled by them not wanting to be in on his scheme, or the idea that honesty has any value to people. The obvious example is that video tape incident with Cliff Main, where upon being discovered, he kept trying to explain how it worked to bring in phone calls or how it was cost effective, and since it was technically legal, and it meant that it was basically a clean scheme to him and he literally couldn't comprehend what his bosses problem with him is.
It even happens with Kim. At this point, he is basically an honest boyfriend, but there was that one scene where he basically forces himself to explain to Kim his predicament (I believe it was him working with the cartel), and you can see in his face that every cell in his body is screaming at him to lie to Kim because the core of his being thinks it's better for him to control her with lies than work with her with truth. He tells the truth to her because she asked him to and because he's basically trying to be a good boyfriend, but it literally goes against the core of his being to just be honest when it seems like lying will be more beneficial.
And that's what I think Chuck saw in Jimmy. That's why Jimmy doing what he does is more or less inevitable. You're 100% right about the other motivating factors, but all that aside, Jimmy lies and schemes and scams because he just...loves doing it. It's passion, it's how he likes to work, and he's existentially miserable whenever he's forced to play by the rules he doesn't see the point in abiding by.