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1. Yeah, I'm aware of this. It's a bad habit I picked up from some native speakers. Given that there is no neutral narration but only interpersonal dialogue and some internal monologuing, however, I'm not too worried about fixing it, because there are people who talk like that. It's technically wrong as of right now but eh. I've come to not worry too much about these technicalities. Because if we go there, the majority of native English speakers funks up a bunch (not using "me/I" correctly, for example).
Also, if I were to write everything perfectly clean, the dialogue would lose a lot of its charm and the distinctions between the characters' "voices" would become way less apparent, because some of the mistakes or bad habits are actually on purpose. Not the one you mentioned, though. That one's just a bad habit of mine. :P

2. It's an oversight on my part but I've known about it for a long time by now. At this point it has almost become somewhat of an Easter egg because I haven't fixed it yet (nor do I intend to fix it anytime soon).

3. That's alright. It's just two different outfits (fight in school and first visit are the same). The one she wearing during her first meet with MC is her everyday outfit and the other one is a jacket and a pair of shorts she's gotten from Reina.

True, the gallery is not possible to fill completely in one run without rolling back. :P
Have fun with your 5th run!