Some would say, that I just didn't play it the right way or that I'm too dumb too play it (or in general) But I'm pretty sure that the game didn't communicate, that you cannot progress further unless you slip in the hotel. Yeah, characters say that a detective shouldn't sleep on the street, but it sounded more like a suggestion. If you didn't ask a character for money (or where to get them) the dialog option may just disappear the next time you speak to them. You can't sleep outside. There is a bench next to a hotel where you can skip time, but after 9pm your character is like "Nah, not doing that". Want to re-read the same book until morning or talk to people? Also not allowed. at 2pm clocks just freeze. Therefore I deadlocked myself of the second day without any way out of it. Again, I understand that it's not an issue for every player, but I was very frustrating for me. So, I'm done.
