AH, the Holy Grail for CD's and TS folks . Well, truth be told, most who say they "pass" or "pass easily" etc, don't really know if they did or not. What they really mean is that they blended in and there weren't apparent reactions to their gender presentation.
Do we "pass" ? No, not very often. Really. I know it is hearsey to suggest this, but ladies it is true. Can we blend in well enough to be accepted ? YES, without a doubt you can. Even if you have a very masculine body. It will take practice ( a LOT ) and it will take some makeup and clothing, etc etc...
Should it matter to us so much ? I do not think so, I'll take acceptance over "passing" anytime. Mostly because the former is so much easier to achieve than the later. There are people who due to their body shape and learned skills DO pass and often. They are rare though.