I'll try to get the ideas flowing. First- we need different careers. They should be musical jobs in nature I think. (Composer/director....soloist.... lead instrumentalist....producer...exec producer..... set designer.... hair stylist....costumer....back-up choir member.... orchestra member...etc. ) If you can think of more- super.
I think that the more prestigious the part, the more the salary...eh? The two end results in the original game are "The Poor House" and "The Mansion". Instead, the two results could be "Lifetime M@G membership" and "Banned for Life" Instead of spouses and kids....perhaps CW friends and CW "best friends" . These are just some starter ideas. More to follow...hopefully.