Cosplaying looks like it'd be fun, although, as
MisaMisa mentioned, it's best to go with something that suits your body type or whatever. Personally, I'd love to pull off a Lulu cosplay. I always liked her outfit, but, there really aren't too many things a person like me could pull off. I'm overweight and African American. Not too many "blacks" in most anime/manga series, I've noticed, so probably no matter who I dress up as, I'll get teased no matter what.
I remember one year, me and two friends were planning on dressing up as school girls and treat the convention as a "school festival", but decided against it a few years ago.
That aside, I don't think that people cosplay as much as the OP is proposing and that only a small amount of people do so outside of a convention setting in probably places like Harajuku like once a week or something.