Something my rabbi told me is that there's never a good time to convert to Judaism. If you've given it a lot of thought and feel it's right for you, take the opportunity. You'll save yourself years of worry and you'll wish you'd done so sooner.
It's the same with transitioning.
Don't wait around for things to improve to live as your true self. The "right time" will never come. You'll just keep moving the goal post and cheat yourself.
I transitioned during a difficult point in my life and wished I'd transitioned sooner. Yes it wasn't easy but it was so worth it.