If you get stuck just ask some of us are very far in the game and have caught up to most of the current content.
I only went for the Shantrel so far. I skipped school for a week when MC said "..but I want more" had the Shantrel in hall event then progressed some further then I kept getting the same events.
When in Kitchen with her in Red Dress, If I give money it goes to fix the Sink then 2 option "Jerk off or Ask", when I click UP hotspot she says don't bother me. I'm trying to get the event where she fall asleep when watching TV but couldn't trigger it.
Best mom poster is like; Red Dress: Sink:1/2, Skirt:1/2, All others are full.
Kitchen with formal dress (I think Monday evening): Under the table: 0/2, Buying panties No 1: 1/2, No2 and No3 at 0. Clean up: 1/2, I want Christmas: 0/2, all other are full.
Bedroom: Only Dream and Bad Dream achieved.
The last picture with her with a book: Only Skip for a week. and Tell her no but where: 1/2 achieved.