I started cutting my hair short, bob-esque, when I was 14 so it's been 10 years of going back and forth between long and short hair.
Sometimes I love my short hair. It's easy to style and drying time is short. Also, it only takes one bottle of hair dye instead of two. And, generally it always looks cute. But there are definite drawbacks. I can't pull it back and sleep-wise my curls tend to get crushed easier than when it's long. And sometimes I get tired of looking "cute". Long hair gives more styling options and I can choose another look.