I Need Hair Help

Ladies. I need your honest opinions. I've been thinking about cutting my hair lately. See, the thing is...I had my hair short for f o r e v e r. And then one day I decided to grow it out. It's gotten really long and I usually love it...but it either takes a long time for me to straighten it (and let's be honest, I'm not the kind of girl who enjoys spending hours on my hair) or I wear it curly and it's just a kind of messy-cute. But when it's short I can only wear it one way. And it's not long enough to wear in a pony tail, so not doing my hair isn't even an option.

Anyway...here's some pictures of my hair at different points. Please let me know what you think! And if you have any other hair suggestions :)

This is my hair a few months ago. Straightened. It's so long and pretty, but takes a long time to make it look that good!

This is last year, but it basically looks the same now when I wear it curly. Just a little longer. 

This is the summer after my senior year of high school. And this is the cut I'm thinking about going back to.

Freshman year of college (that's me on the far right)

That's what it looks like if I wear it curly.

(Not cute)

Here it is curly after it had grown out a bit. Still not that cute but better than it was.

A little longer...

Medium length and straight.

I just don't know what to do! I just want easy, pretty hair. Is that so much to ask for? ;)

Please help a sista out!