1. I can't really help you without a picture. There's only so much I can imagine from 'skinny', 'pale' and 'round face'.
2. Nonetheless. If you think you can do it then just go for it. A lot of anime guys are cosplayed by girls anyway and like I said: if you think they can do it, go for it.
3. There are a lot of threads around here (and on the Internet with the help of google) that will help you with crossplay from binding to make-up to whatever in between.