Spend the first 5 days purely working and studying. Accumulating $500 early makes the rest of the game much smoother.
Focus on Intelligence (study at the library) and Strength (gym) to unlock specific dialogue options and events. Main Character Routes (v1.09) The Sister (Main Plot) Become Someone [v1.09] By Volen
Attend classes daily and stay late for "extra help." Spend the first 5 days purely working and studying