I hate the whole chair experience too, and the way that 'tidying up' can become a fucking crew cut in the wrong hands.
I refuse to do the hairdresser thing, as if I wanted to pay for somebody to try to shove her tits through my head while giggling and making inane conversation in the hope of a hefty tip, I could have that done in the knocking shop up the road and still have change to go for a short back and sides. I've also suffered the results - super high-maintenance hairstyles (an hour just to get it looking acceptable) which look good on Japanese RPG characters but like utter shite on yer man in the street.
In the past, I've left it pretty long and Brylcreemed it back, letting either a girlfriend or a female friend trim it when necessary, or carefully applying the clippers to myself. Periodically, I would shave the whole thing off, and keep that look for a while.
Recently I've been using a decent barber's shop who will actually listen to what you say and also make suggestions. So I usually have some pretty badass pompadour look going on. Are you happy now, ponch? :D