| Any woman becoming a man would, obviously, have spent her whole life as a woman and she'd suddenly find herself in a whole new world with radically different norms, social expectations and morals. She'll be still thinking like a woman, due to her rigid training in womanhood she got from everyone she's ever known while growing up and when she steps into The Man Club, oh, she'll be shunned. Boys generally tend to prefer their fellow boys to be as or more manly than they are. Don't ask me why.
Of course, this speaks mainly for the more feminine women or the girly girls. She may have been a tomboy, she may have prefered male company to female company all her life but I'm going to take a wild guess that she won't like actually being one. She might even have a dabble at a bit of culture shock or at the very least an uncomfortable feeling of alienation.
What else would there be? Choices in what to wear would be radically reduced making the whole process infinitely easier but, as far as I can see, not as much fun. This includes a need to donate a whole bunch of shoes to charity, replacing them instead with one pair that goes with fifty percent of her wardrobe, and another pair for the other half. She'll have lost a good portion of her sexual allure and have to take a lot of the responsibility of approaching people in the dating game.
Since boyish girls are generally more accepted than girly boys I'm not so sure that, purely in terms of social interaction with their recently same-sex peers, the reverse would apply. Of course, the guy that wakes up and discovers he's switched sides will have his own big bag of 'problems a-plenty' with his name on it to deal with. :)
It just goes to show, doesn't it? Biological sex is just a small portion of who someone really is. It's what's inside someone's head where it all goes on.
note: if any scientists need funding to research technology in turning guys into girls and vice versa to test this theory then i'd be happy to do a sponsored fun-run or something... ;) | 
