Hello Anatta
Oh that is a good question.
I read somewhere that 90% of the people who begin transitioning fail. That's a scary number.
To succeed I think you need all of the above, and the emotional reassurance of a healthy pile of cash probably helps too.
I feel like I have all of the above in reasonable quantities at the moment, which is surprising because I was neither a confident person nor impervious to criticism in my previous life.