yeah, i'm not smart enough to figure out the correct strategy, so i can't second guess some one else. my gut is that it is better to be in DIII than DIV, simply because more money means more options. for that reason, i commend your foresight.
for myself, i set myself upon a path that involved a lot of training, and keeping an all-Utopia team, so me advancing is moot for a couple of more seasons. if i am going to buy Utopian superstars, i have to train them!