About bugs:-
1. Any idea if it's a quest dialogue or normal one.
2. Well there was a bug with her before but this one isn't. It happens because NPCs follow you after a distance threshold. Since Masuo is slower in this case they reach him and stuck in that walking loop.
3.Will keep note of that.
4.It doesn't happen until you are in live stream phase of her quest. May have problems if you did Timeline 2 quest before tennis one.
To answer your question.
1. I want players to try out different outcomes of an quest without losing items from that quest.
2. Do you mean deleting all cloths? Yes. It will be available in main menu.