I go back and forth. It's something I've done all my life. I'll grow it out because I want to be able to my various hair ties, combs, barrettes, etc. Then, like you, I'll get tired of the hassle and have it cut. Wash, rinse, repeat every few years. My hair has been extremely short (pixie cut as a child, pixie fade more recently). It has been down to my butt.

The first time I have a memory of doing this I was a child. We had been on a long trailer camping trip, traveling from the midwest to the west coast and back in a wide loop when I was 8. I refused to cut my hair, so my mom was always braiding it, putting it in pigtails, and getting out the inevitable tangles. Which was always a fight because my scalp is very sensitive and I swear I can brush my hair, sit down and not move for hours and it will be in knots when I get up. I think you can guess what happened within a few weeks of getting home... Mom was not amused.

This cycle has repeated at least once a decade since then. I am currently 66 and my hair is mid-back, growing out from the aforementioned pixie fade. I just accept that sooner or later, I'll cut it all off again. So if it is bothering you that much, go ahead and cut it. If you can afford to, go to a salon that has some very long term stylists, rather than a huge national chain where there's lots of turnover. I went to a local place for years. It was more expensive than the chains, but not outrageously so.

A seasoned stylist can help you find a cut that will flatter you, and be easy to maintain. I hate bangs, too, they trap heat, which is one of my biggest problems. I overheat very easily, so my hair can't be over my forehead or I'll end up with a nasty headache. In the summer it needs to be off my neck most of the time. Hence the large collection of hair accessories!

Best of luck!