It does suck that the imo the hottest of all the women is the one who is in the NTR path. Like why is Madison in the program? She is in a committed relationship. One can obviously think of reasons she wouldn't want to be with Jake's brother and get impregnated by someone else, and I don't think I'll enjoy any of them.
However, it makes sense that Jake gets less money since as another user pointed our, men can just pump and dump and see many partners with no risk of pregnancy while once a woman is pregnant she is out of the system she is no longer earning.