I think the biggest issue with the hint system currently, IMHO is that sometimes it will give you a hint that you can not use, due to some other prerequisites locking you out.
I've seen this often with "what should I focus on next" and "I need hint" -> "Fun points".
For example, before I got 2nd level of persuasion (getting from joining Hannah's class), it would often give clues about stuff that is impossible to do until getting that 2nd persuasion skill point.
"One of the main characters" and "One of the days" options are in much better shape and rarely have this issue. One problem I have with them is that they often spoil the story. Giving you topics that the player did not yet even encounter. Then when asking about them telling you to advance other parts of the story. Why even have them present as a topic, if currently locked out??? It just makes it difficult to find out topics on which you can actually act out currently.