I would have gotten into a LOT less trouble in nursery school/kindergarten for playing with the boys.
I would not have been taught how to cook or sew.
I would have been required to learn talmud at a young age
I would have been sent away to school in the east coast in seventh or eighth grade
I would not have gotten a reputation as an oddball for insisting on dressing in black and white, wearing lace up black oxfords, and modeling my brother's black hat in the mirror.
I would not have been allowed to go to college.
Ok, so my life was weird even without the gender issues. But in some ways, my tendency to cross-dress a bit--wearing severely simple black and white clothes, and white oxford shirts--as close to Orthodox Jewish men's clothing as I was allowed to get--was met with approval because it was "modest". I didn't push the envelope in quite the same ways as my classmates (all female, strict gender segregation), and so I didn't get the same level of constant harping about modesty and such. I was a young prig with a seriously overdeveloped sense of propriety. If I had been born a cisboy, that probably would have earned me a spot in an elite yeshiva at a young age.
Boy, was I lucky to have been born female. Ironically, despite the oppression of a strictly patriarchal community and marriage model enforced by the community, women before marriage in that community have a lot more freedom with regard to education, and education is the key to getting out.
After a year of attempted brainwashing in Jerusalem I went to college and I even got my first pair of jeans. At the age of 22.
When I say I'm ambivalent about my sex, boy do I mean it! I doubt I would have survived long enough to escape if I had been raised a boy.