I haven't read this whole thread because I'm on my first playthrough and was starting to see spoilers, but here are a couple of things I noticed so far:
1) I was confused about the going to work screen.
The screen shows $Charisma for waiter, and $Knowledge for cooking.
At first, this made me think that I could increase those stats by doing those jobs, not that I needed those stats. Maybe add "Requires" to that screen? Not a big deal, but a little confusing.
2) The first time I went to bet with Yui, I only had $127. I was able to continue (and win) even though there was supposed to be a $200 minimum. It should have said "Come back when you have enough money".
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*play it off