You're welcome ^-^ Your game has quite a special place in my heart as a genuinely fun game.
With "annoying Cassie" I can't seem to find any other thing to do so. I've talked to her a lot (clothed), talked to her a lot (naked), given her Devil's Milk, but can't seem to trigger anything. Other comments I read were saying to talk to Cassie about Alissa but the only "Talk" option I have is "Ask about being bought". Possible I'm just not annoying enough which is a surprise given how much I enjoy torturing her :/ I'll try annoying her a bit more though.