My spouse's story is similar to yours--a history of depression, but didn't hit upon transitioning until recently.
From my perspective, I think if you look in the mirror and want to see a female face looking back at you (sans makeup etc.), then transitioning is most likely the right choice for you.
From my experience, I feel issues of being feminine or a social role really fall away, because ultimately, what's going on isn't about being feminine or a particular social role, it's the face you want looking back at you in the mirror.
<3