Introduction - Birthday Party & First Day of Work:
1) Find Rachel in the garage.
2) Find Summer in her bedroom upstairs.
3) Return to Danielle/Vivian
4) Go to Sleep

Danielle's Questline:
1) Finish the Introduction.
2) Spy on Danielle while she's in the shower (Afternoon - Backyard/Backporch)

Rachel's Questline:
1) Finish the Introduction.
2) Once you've received a text from Rachel, sleep a few days until an event triggers.

Summer's Questline:
1) Finish the Introduction.
2) Once you've received a text from Summer, visit her in the evening in her bedroom.
3) Return to Summer once she notifies you that your painting is ready (Once completed, you can commission more paintings from her).
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SideQuest Content:

Simscape - Video Game Scenario:
1) Purchase the game at the "Thrifty Pawn".
2) Install it on your computer in your bedroom.

ShowerThoughts - Imaginative Lewd Content:
2) Take a shower in the spare bathroom (Upstairs).
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Tips:

Loose Money Locations:
1) $20 - Lying on the dresser in the Master Bedroom.
2) $30 - Hidden in the box in the Laundry Room.
3) $20 - Against some boxes in Veronica's Office.