I found the writing to be really well done, I love the humour and even though I've never played a visual novel before, all the little choices really kept me around.
I was a little confused though about the whole roulette thing when choosing, whether that was a reference to the fact that the character has gambled their money away, or was something else.
I loved the music, it was genuinely really nice to listen to the whole time. I'd suggest that maybe some sound effects for characters appearing could make the experience more engaging, possibly some sound effects for different things (bumping your head, car revving).
I also found a bug on day 3 where I was called "playername" for a couple of sentences. Good job, my first ever visual novel!