Funny, I'm doing the opposite right now. Kept my hair short for the past five years, sort of doing the opposite right now, though it's a bitch to clean and I don't think I'll be sticking with it for long.
There is a time in the process of not-cutting your hair (which it was for me, as opposed to purposefully growing), several months of it, when it's not quite long enough to put it in a ponytail on the back of your head, but long enough to get in your face, like, all the time. I was preoccupied with loads upon loads of stuff going on in high school, so it didn't cross my mind that much. For others, I suppose it is something to endure.
From there on though, it's brush-wash-twice-a-week-ponytail-forget.
Thinking about dying my short hair red, actually. Not sure if it'll work for me, I'll think on it.
Yeah, that part is the worst!! Particularly when I was playing racquetball - sweatbands are useful anyway, but I absolutely required them at that point, because otherwise sweaty hair flayed my eyes. It's as horrible as it sounds. I even wore shades indoors a couple times but the hair still gets in the way.
Kinda a shame, because it's otherwise convenient and kinda cute. But ponytails are also pretty easy, particularly if you like hairbrushing like I do.
RIP your hair, though ;_; I say go for the dyes, make the most of this! Having pink hair was actually a lot of fun! I kept forgetting about it, which led to people being impressed by how confidently I wore it XD
And colored fringes can look really neat...