Hello! I think you may have missed the tips that occur when you start the game.
To begin story events, they mainly begin at their door with " *Talk* " options, especially at the beginning of the game. Asking "How are you?" will open up dialogue on how they feel about what happened recently in their story. It should also be noted that stats have no influence over the story and are for additional side content. Story events pop up on a cooldown, and the game will tell you if you need to do anything extra.
Pinups are an option that appears after you click on a character in their room, it may be greyed out for you early in the story though. Clicking on it will tell you what you need to unlock it.
While pinups are a decent way to make money, there are also Deliveries from Bernie's Bowling Bar. Building the garden, and building a bar of your own are the best ways to make money.