I always tend toward letting others do what makes them happy/what they must do in order to get by. Life can be tough even if you have it all; if you are less fortunate in some ways (not passable, living in a dangerous area/country, not having a good job or a lot of money, meaning if you lose your job, you'll be skrewed, etc), I will not judge you if you have to drag in work or social situations. If you are transgender but you cannot express it outwardly, then that's your business and right, and you'll get nothing from me but my blessing.
Personally, I move between a very liberal city and country and a very homophobic country twice a year, plus a lot of travel to inhospitable countries in between. Since I am not (and am not interested in) 100% passing, which is what I would require in order to be physically safe, and I am not willing to curtail my travels (as opposed to moving to say, san fran, and letting it all hang out as I want all the time), I compromise and get back in male drag when I have to. I know what I am on the inside, which is a full time woman who sometimes has to drag as a male. To be looked askance at that choice by a 100% passable transgendered girl is as silly as if I were to suggest to that same girl she's not doing it right because she can't afford her SRS surgery whereas I could, and did.