I love the writing. It leans hard into the trope and kinks. However the game itself needs a little bit of work. Don't get me wrong, content is always preferable to filler, but there is also too much empty time that is unfilled.
Perhaps you are leaving space for additional content, you are implementing repeatable events in a later release or you reverse coursed on some sort of grind mechanic, all of which are very valid. But having to 'search' for events just to realize there is nothing to do but wait/sleep is a little frustrating. You should never have 'wait' as the only choice for the player. Whether it is grind money or train a skill or contemplate the meaning of life, the player should always have some sort of activity that gives the (false) sense of advancement. As it stands, you are making a VN and putting it in a sandbox.
Keep up the good work though. Look forward to future releases.