Seems a lot of dudes are confused on how you progress and the grindiness of this game.
Progress: Just skip school. Don't bother with the riley questline, its not done. You want to stalk to blonde chick until it stops giving the option. Then spy on your mother and sister in the morning in the shower, then the last sister about 7:20 in the evening. Then buy a microcamera, spy on that last sister to steal her key twice and plant it in her room. This seems to be the max 'discipline', the most important stat.
Once this is done just keep checking agendas and spamming whatever is says to do until it actually works
Fitness appears to do nothing but add repetitive grinding.
School may be important, but I'm not sure if the study option vanished because A: there are only 1 series of tests or B: I romanced the nerd chick. Since you can still 'study' with her. If its the latter, please don't remove the one from in my house just because she's also available. Its a lot more clicks and time limited to study with her.
Aside from this, the writing is... questionable. The vocab used is very stilted at times. Doesn't sound like how people actually talk.
I've also noticed it mixing up he/she quite a lot.
Even if you ignore the ridiculous fitness grind and showering every day for charm (a stat which both raises far too slow and appears to do nothing) and the absurdly low paying jobs (just buy the DIY book for the milf next door and camera, ignore everything else), the game just has a ridiculous number of clicks to do anything.