Your friend doesnt approach girls because he fears rejection, and he rationalizes it by tellinf himself that hes not good enough for her anyway. Its called a limiting belief, and they are detrimental to game. Im guilty of it myself.
In general, I stick with "my league." Im a blue collar worker, with a blue collar car, and a blue collar van. If there is any truth to your statement, it would apply only to serious relationships, and/or marriage. A rich lawyer chick, probably wouldnt see me as relationship material, but she would probably fvck me, and maybe change her mind about me later. There is a respect issue that would always be there though. A woman will respect a man less, if he is in a league below her, but it can be overcome, if you make up for it other ways. Your friend should approach any chick he wants. Give the woman a chance to make a decision about him. I've dated girls out of my league before, and it was tough because I didnt possess enough true confidence in myself, and it was a recurring issue. She didnt respect me, and I was never introduced to her high class friends. She's dated movie directers, pro athletes, millionaires, and was financially set for life, and I bring home a seven hundred dollar paycheck a week if Im lucky. Obviously I couldnt afford to do the things she was used to, so she would pay for anything I couldnt afford, which was a blow on my ego. She said she loved me for me, and money didnt matter to her, and for the most part, it didnt, but it did.
Case, and point, low class guys can date high class chicks. There may be problems, but it can be done. Im sure there are plenty of lower class dudes the have healthy relationships with higher class chicks. Plenty of dudes have sugar moomas too.
Its all in your friends head. One of the things we should all learn here, is to recognize limiting beliefs, so we know we need to ignore them, and go for what we want anyways. The worse thing that can happen is you get better with the practice of gaming high class chicks. The lower class ones will be all the easier.
Edit: There were other posts as I was writing this, so I'll add that I am a starving musician also.
And, women look for the potential a guy has. For example, Im a painter. I can start my own company some day, and make six figures a year. My current boss collects corvettes. Im no different than him, I just haven started my own gig yet.