Under the progressive religion, trooning out would absolve Chibi of all his past sins (eg his falling out with his close friend), live life under a new identity unburdened by what has been and he will be welcomed by the rest of the leftist cult. So that's one incentive for trooning out.
So why hasn't he trooned out? My guess is
1) his humiliation fetish (eg the infamous GDQ incident, the open fly/buttcrack on Japanese television etc)
2) he enjoys playing the victim and whipping himself in public for pity points (eg I regret what I have done, I must do better, please support me).
3) He is a red-blooded 100% heterosexual male and he's only interested in cosplay pussy. He only gives lip-service to his claims of being bisexual. Libshit women, even if they support the troon ideology, are disgusted by fem-presenting troons as romantic interests. Trooned out Chibi would destroy any chances he has of getting girls and he would have to resort to other troons (but as I said, he's not interested in fags).
4) He's just fucking lazy and doesn't want to put in the effort of chopping his dick off and dilating and taking HRT and all that troon shit