I never repeat things if they don't progress if thats what you mean. Still I could probably train all week between two events and not even progress anything else. Like I said, hopefully at some point someone will create a WT, currently it's just way to intransparent.
What i meant is, if you ignore training because you want pussy, you'll get crushed by more powerfull than you. It's not a "either or" situation. There's a set amount of times you can use the training option, it's not infinite. After that, when the option stops being there, that means you've done all the training you currently can, and there's nothing else to do than character stories until the main plot moves forward enough.
For example at one event with Emily and her dad I got the choice "don't offer to pay the bill". I suppose I didn't had enough money to get another option? Showing that other option grayed out with an hint how much money I'm missing would already be helping. However there is no way I go back hours of play time to the last time I spend money to try and have more money during that scene. Don't know if I'm missing out on anything there but how am I supposed to know. The game is completely intransparent on this.
Some money falls onto your lap later on in the story. Though, admitedly, it's hard to tell if you go for Emily right away...