One thing you guys are forgetting regarding why Russ wants to become rich and famous with a sexy 9/10 pop starlet on his arm: he desperately wants to prove to everyone that they were wrong about him. He wants to show his biological parents that they were wrong to abandon him. He wants to show his adoptive family, former friends, former teachers, and former bosses that they were wrong to tell him he couldn't accomplish the goals he set. He wants to show all the girls who rejected him and the bishop who told him he probably wouldn't find a super hot wife to marry in this world that they were wrong about him. That is the big driving force in Russhole's life: to prove to everyone that he can make his dreams come true, that he can become famous/important/successful, that he is someone who can attract the hottest women.
That's the big motivator behind Russ paying for the girlfriend experience with prostitutes. It isn't because he wants to feel like he's "earned" sexy time with them, because in Russhole's mind he already DESERVES it. It's OWED to him. No, the reason Russ likes taking whores out to Olive Garden is so other people can see Russ with good looking women so they think he's someone who can attract women like that. In Russhole's mind he deserves to have women like that on his arm and have other people see them with him, but until Taylor Swift or some other hottie finally comes to their senses and starts dating him willingly, then he will happily pay for a woman to accompany him out in public where they can be seen together and have people assume that they are a couple.
Russ doesn't care about earning things, because in his mind he already HAS earned them by being disabled and living the life he does. If Shit-lips actually did care about earning things then he would be working hard using every free minute to improve his song writing skills, learning musical theory, and getting connected with local bands to write music for them in the hopes that it will get more ears to hear his songs and hopefully get discovered by someone in the music business. But that's not what he cares about. He only writes songs for famous women in an effort to stand out from everyone else who is trying to get their attention. It's kind of like a Trojan Horse to sneak his way into their regard. He hopes that they will recognize his "efforts" to gain their attention, hopes that they will feel "flattered" by the gesture, and that they will see him as a special, unique soul who is worth inviting into their lives. It isn't about earning his way into their life (and their bed), so much as he uses them as a shortcut or cheat code to get what he wants faster, because he already deserves it just by being Russell Greer.
As far as the jobs Russ has worked, well having a strong work ethic and making your own way through life is a big party of the culture surrounding Larter Day Saints. We value and appreciate the pride and sense of accomplishment one gets from an honest day's work. We also value being charitable and helping out the needy, which is why most members will pay a tithing so the Church is able to help out those in need. On the other hand, we believe in being self-sufficient and making our own way in life, and to only accept charity and welfare only when it is absolutely necessary, and only for as long as necessary until we are able to get back on our own feet again. Russhole likely learned from his parents that he needs to do everything in his power to stand on his own two feet and that living on welfare is wrong. I don't think he gets any sense of pride or accomplishment from working hard, he just does it because that's what you're supposed to do and it's the only way he will ever get the things he wants (like affording brothel trips). Plus I think his ego would keep him from ever getting disability, because that would mean admitting something is wrong with him and he's not the incredible, infallible person he believes he is. Going on TardBux would mean Russ admitting that he's a retard, and his ego won't allow it.