It sounds like your hair is VERY damaged if you have so many splits, so a big chop is definitely in order, IMHO. I think you can pull it off- you have to think of it this way too- you already wear your hair in a pony all the time, so your face is already exposed, so it won't be much different. And if you want a change- there are always wigs! I know it sounds crazy, but there are some seriously cool wigs in hot pink, black, ombre, you name it. When I was in college I had this friend who had a pixie, and a huge collection of wigs, and she was just cool, you know? I never knew what she was going to look like on any given day.
ETA: The cut you showed the pic of would require serious straight-ironing to achieve this look, and you would end up with damaged hair again. I would say to keep it curly and learn to pamper your curls...either go pixie short, or go slightly longer since your curls will shrink up.