swimsuit2.png and sport.png are only available to students so it makes sense it'll bug if the game try to make other characters wear those. But this shouldn't happen so definitely a bug I'll look into.
I see some embarrassed/casual.png which also shouldn't be possible since only the naked version should be used. Strange.
And finally, many max loops reached. Bug in the AI which is tricky to debug but I'll investigate more in the future versions to eradicate this annoyance. Some of them seems simple mistake with the pathfinding not being correct, should be easy to fix. Other with destination unknown are stranger, there should always be a destination and if not, I coded it to stop the loop to avoid wasting time. Strange to see this error. I remember before this error happened when skipping several hours and reaching a new day, the AI was only working on a 0-23 hours of a single day and failed to find the schedule for the next day. I thought it was resolved but since you say you get error during a new day, it might still be there. I'll check it.
In any case, thanks a lot for the feedback, that's really helpful and I'll do my best to fix all of this asap.