If it is society's acceptance you are after, it would be easiest to present as the gender that you display physically.

Society's preferences will clash with your own in this regard. You have to decide the extent to which you care about that. Societal advancement is slower than technological advancement, and it is likely that the technology to pass completely will be available before society gets to a point where they do not judge people who don't fit gender roles.

Have you tried presenting as the "other" gender socially for a few months? How did it suit you?

Also, have you considered that you might reverse the transition, if you change your mind? (Assuming you have the money)