A friend of mine found this out on the web, and I'm fascinated by it (check out the "blog" link to the left, too...hit "newer entries" when you're at the bottom--so far the character is up to day 30 or so in entries).
From what I can see, they collapse having a vagina with having a feminine outlook on the world. Somewhat troublesome ideologically, but I get the feeling not done maliciously, here. I have a feeling, instead, that girls who see this might feel vindicated in some ways seeing a body that has all the visual earmarks of being male having to deal with some of the little aggravations and emotional issues that they have to. If so, then that makes it an incredibly important text (especially for a YA audience).
There are a number of books out there on gender switching (both adult-audience-oriented, and YA) Cycler by Lauren McLaughlin. The book was not too bad, but the ending disappointed in a big way. The one thing it does that "Zack." hasn't done yet, though, is very frankly discuss sexuality--I'm assuming that's coming, though.
This really puts me in the mind of Tiresias, the blind seer who spent a while a a female in order to know the world more fully as an oracle.
So far, it appears to be a web-only show, but from the looks of it, I think this is a viral marketing build up for an indy film of feature length (just a guess). Here's a review