My hair is too coarse and dense to go short. I did go really short about eight years ago, pre-CG days, yet it was awful. I have a very curly spot in the back canopy which needs length to tame it. I know I am not sporting the best look now since I wear it back daily but it is more manageable for me. It seems the longer it gets the better I can manage it.

I think a gradual change to shorter hair is the best approach. Maybe you can get a cut that is still long enough to pull it back, yet short enough to give you an idea if shorter hair would work.