Here is what I've found so far:
Each girl can earn money once a day (use phone booth/female washroom in school to switch char (1st option) or change clothes (2nd option).
Once both girls have worked, it will be sunset. All the events have 4-8 scenes.
You have a quota to meet each week, 1st week is $50K, 2nd week is $80k. Missing quota = GoR,
Nanami (Brown Hair Girl)
Book Store ($4k/day), require School Uniform
Maid Cafe ($9k/day), require Maid Outfit
Massage Parlor ($15k/day)
Office Lady ($20k/day)
VR Game Testing ($6k/day), require H level to unlock
Prostitution (Phone at home) $15k/hour, require H level to unlock
Other:
Ride bus to home in the afternoon (sunset), require School Uniform
Photo Shoot in school ($5k if successful, spanking if caught by teacher/GOR if caught 3rd time)
School Counseling with Teacher (unlocks after a few days)
Marina (Orange Hair Girl)
PC Cafe ($3K +10K tip/day), require casual clothes
Clothing Store ($5k/day), require casual clothes
Adult Toy Store ($8k/day), require sexy outfit
Gym ($9k/day), require leotard
Bar ($9k/day), require H level to unlock
Photo shoot ($10K/day), require H level to unlock
Other: White Hair Guy in school yard, after talking to him a few times
You can also rest in the inn to spend $2K a day to manage your income.
In the afternoon, there is a sparkle area east of the gym/book store that you can use to forcibly raise your H Level.
As the story progress, the black hair girl (the "friend") will start giving H events.
You can find her in the classroom, and neither game must not have done anything that day in order to trigger it (one exception, you can still trigger School Counseling with Teacher)