I love long hair, you've done 3 customs for me in the past that centered around getting mess all over your hair Personally I wouldn't go any shorter than the shoulders...That being said, you do whatever you want, it's your hair and your life. I get that long hair can be a bitch, my hair's down past my nipples, I haven't thought of cutting it yet, but I definitely see where longer hair can be a drag...takes an hour to shower, dry, and style for me, usually try to go a week without washing,
but lately it seems like it's twice a week ever since I switched over to using a bar shampoo as opposed to bottle.

Whatever you do, get a Good Dye Young lightening kit and go purple! Their Purple People Eater dye is boss haha, I can make silly suggestions right? I love it. I've been using it for a couple years now, I have a stash of it in my closet

Even though i vote for keeping it long, I'd love to see you with pixie cut

You could cover your pony with a messy substance before cutting it off, which no one would ever do because it won't come out... and then you "have to" cut it off (like a show,as punishment)

Such as varnish, super glue, paste, tar. Pu foam

Regarding hair color ideas, what about dark red such as Dana Delany or Angie Everhart?

I would vote for the last two longer options you listed, I too have long hair, and realize theres more maintenance, but clean or messy it adds to the appeal =)

I like all the movement that comes from shorter hair. Longer hair tends to stay in place when it's wet/messy. looks like the people have spoken, and I agree! shorter hair would look amazing on you and personally, I do buy more scenes that have shorter hair.

If you cut off a fair amount, there are charities that makes wigs out of donated hair for children cancer patients.