I apologise for some parts of the game still being more obtuse than I anticipated ^^;
You can go to near where you spawned in the city to return to the hubmap where you can find the door to her house to sleep (it's on the other side of the building behind you when you first spawn when starting the game).
The lack of money might be to do with not having fulfilled the "requirements" on the left. You can still make money without them, but you get significantly less. I'm revamping this system in the next version to fix the lack of clarity there in addition to other things about it.
I'll definitely try to address the clarity issues with nighttime and sleeping in the next build, especially as it does intersect with the gameplay changes/additions I'm working on
Once again I apologize for how obtuse it is, it sort of slipped my mind while I was working on the core gameplay systems ^^;