I've never had long hair, in the sense of it going down my back. But I have had pompadours of varying length and height, culminating about 2 years ago with an 11" long pomp. Glorious hair.
It drove me crazy...maintenance, washing, primping, preening, and I couldn't walk down the street without my hand pushing it back up and out of my eyes. My hair grows naturally into a pompadour, but at that length it was unmanageable.
So I got a crew cut. Which my barbers then suggested I change to an increasingly short flattop.
I currently wear a very extreme, shaved, US Marine style horseshoe flattop...and have never looked better.
Having had both, I can confidently say that short hair ROCKS!