I NEED your help!

I have a major dilemma... it's called hair. You see, I never know what to do with my hair. Pretty much, it either goes up into a ponytail, or, I leave it down. I always see these people with long hair with the pretty curls and think "Oh, I want my hair to look like that!" but my hair doesn't curl. Well, it curls, but it doesn't stay that way for very long at all, and it takes forever to curl it. So then, I'll see people with these really cute short haircuts, and I'm like "Oh! I love that!" but then that would require me to actually do my hair! I know, right?! Plus, when you have short hair, if you want it to stay short you have to keep getting it cut. You see, when it comes to all of this maintenance stuff, I'm horrible. I haven't had a haircut since the beginning of February. Before that, I'm pretty sure it had been over a year. I just really hate spending money. So, I have this habit of chopping my hair really short (because I don't know what else to do) and then growing it out for a while until I get sick of it, and then I chop it again.

Am I the only one in this vicious cycle?? It sure seems like it. Everybody else has this really cute hair that they curl, or they put in buns, or do other fun stuff. And I'm over here like "hey, at least it's in a ponytail today!"

I'll cut to the chase though. I need your help deciding what to do with my hair. This is what it looks like now:

This is what it looks like when I cut it short (Please excuse the stiff arms):

This is what it looks like about shoulder length, and what it looked like in February:

Also, I should mention that bangs are out of the question... I can't stand them on myself. Also, I probably won't do anything drastic to the color, because you know, if I color it then I have to worry about roots and stuff... Anyway, it just feels so plain right now. So, the question here... to cut it, or not to cut it? If yes, how should I do it? Let me know.

Thanks for your help!