Wow, this post got me really thinking! For the reasons many of you have mentioned, I do not think this would work out for most people. In my case, I think I would give it a try.
Here's the thing - I'm a gemini. I do not really give much credence to astrology but my personality definitely fits that profile - I like to experience both sides of everything. As such, on more than one occasion, I've been annoyed by the fact that you only get one life and one gender. I'd be insanely curious to know what life would be like as a girl. For that reason, I'd be fascinated by my female self. Would she wear the cute clothes I find attractive myself on women? How would she style her hair? Would she be goth and wear twin tails?
Since she is, well, me, she herself would be intensely curious of my life as a male. We would probably talk for hours about how that one tiny variable, gender, makes a HUGE difference. Just think of all the many differences between males and female - different body shapes, different clothing, different ways of reasoning.
Would it work out? Who knows? But, I do know my female self would be just as curious to find out.