To paraphrase one of my favourite captains, there is only what one can do, and what one cannot do.
If you feel that transitioning will make you happy, and that it's a path worth pursuing, then it is a path worth pursuing. If you feel reserved, and cautious, then you should likewise be as such. And finally, if you don't feel in your heart that any of this is what you want, and you are merely searching for what may be right or wrong, then perhaps it's all worth forgetting - we all have the right to pursue our happiness, and by the same token, we all have the right to abandon a pursuit that would lead us to unhappiness.
Do whatever makes you happy, and you will have my support so long as your actions don't affect the freedom and happiness of others.
And to Hell with the details.