I cut my hair in May this year. It was almost down to the small of my back and like you always tied up. My hair is very thick so it always felt so heavy. I went for a shoulder length bob but had the back cut shorter then the front for something a bit different.

I LOVE it!! Do not regret it at all. It is still long enough to tie up, or short enough to quickly blowdry. Most of the time I put a bit of curl booster in and leave it out with a bit of the front pinned back (also had fringe cut but I am growing that out). DS is over the hair pulling stage now but when I first got it done he would pull a bit but because it was short he would usually slide off my hair.

I say go talk to a hairdresser or two and decide on a style that will suit you but will be easy for you to maintain and go for it.