Hair help

I get into this hair rut every few months when my hair starts growing out. I always get it cut short, and then can't decided whether I want to keep it cut or let it grow and then once it gets to this middle stage and complain about it everyday. So once again I'm there and can't decide if I should cut it again and let it keep growing out. You can see how it looks in my previous posts. The pics from the rodeo, it was not really fixed, just shampooed, brushed, and air dried. The pics from Graham's dedication I actually blow dried it. Not much of a difference really. If I got it cut short, I'd get it like this again

This is how it looked at it's longest. I got it cut just before Erica's 1st birthday, so over 2 years ago.