Is it weird that I would want a therapist who had also taken psilocybin? Preferably many times. It feels like it would be demeaning to have someone who approached it in a clinical and proscribed manner.
I'm not sure what the criteria for getting certified to do psilocybin-assisted therapy are or will be, but my guess is they'll probably be pretty similar.
In general, at least for now, it's pretty safe to say that most therapists interested in doing psychedelic therapy are already interested in psychedelics and probably are already "experienced" or will be during training.
For me, much more important than if they've had a psychedelic experience is if they're highly recommended by well-informed people who've gone through therapy with them and who I trust. If they green-light them, I'd feel much more secure.