Thanks for your detailed commentary, I really appreciate it :)
You have some good suggestions, I'll think about them. Especially number 3, Liz, Mira, Kat, and Ann should have different phrasing for that mechanics, great idea!
And on the guild quest, I'm currently planning on making a progression on their quests which will be added on a higher ranked quest when they're available. For example, in the character your mentioned, her first quest is training her to have a conversation, then her second quest will have her try to talk to strangers, her third quest will have her turn a classmate to a friend, and so on.