I am not sure you realize that part of success for relationships is accepting people as they are. People don't like the bait and switch of "you're wonderful!" and then being told "you're wonderful but I need you to do x, y and z to keep thinking so" Chipmunk was invited into your home as is because nobody took the time to know her, and now she is being told who she is isn't good enough (dont' get me wrong, I wouldve said long time ago - made a mistake, youre wonderful but I can't live with you because we aren't compatible that way). I hope that in the future you take the view that people should be accepted for who they are, and if they don't mesh with you as roommates, friends or lovers, then don't have them be that. If they aren't mature enough to be in a seriously complicated relationship, either dont be in one or accept that they are flawed. I don't imagine if Wolf gets involved with an older person you would like to hear they are being told they need to do this and do that and grow up in order to be good enough to be in the relationship.
I'm kind of sad that you glossed over my advice about it being you and Airyn that you should be focusing on. Airyn is the hinge and he's the one who should be willing to do the buttload of the work, and so far I haven't seen much but cowardly behavior from him and letting you do most of it. I know its easier to tell other people to change because that's easier than working on yourself so it feels like a possible easy fix. If you expect Chipmunk to change overnight, maybe you should do it first to set an example. You and Airyn seem so caught up keeping the emotional drama going (not on purpose, just not choosing to step out of the whirlwind) that doing the basic groundwork which would possibly fix the majority of issues you have must not seem interesting. Without making firm time and space for you and him to be alone and being together, you allow the issues with Chipmunk to be present even in the rare times she isn't.
I really wish you guys luck but I think you could do a lot of stuff you're not to set yourselves up for success.
Happiness will never come to those who fail to appreciate what they already have.