If by fresh start you mean start a new game, I did not (Going to right now )1 - did you have a fresh start?
2 - can you share your savefile?
Here's the save that has the issue:
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EDIT: Finally found the issue. Afer the first training with Reiko I generally use the sleep function to skip the night hours, but that apparently breaks progress. This time I just used the wait option several times and now I got the proper event after training 3 times. I didn't realize sleeping instead of waiting would break the chain ( I doubt it is intentional at all). So mystery solved, now let's see where the story goes given that what I've played 4 times so far is right up my alley, haha.
EDIT2: Right after the cutscene i was supposed to get I get the hint to sleep in my room and yet again it triggers nothing. Please tell me I didn't mess up again?