Chuk used to get his hair cut at those $13 walk-in places, which was fine. He cut my hair, which was, until fairly recently, just long and straight. It was easy for him. All he had to do was cut a straight line across.
At some point, I don't remember how or who brought it up, we decided I would try cutting HIS hair. Boy hair is intimidating. There are "machines" involved. But Chuk's not very vain and I am pretty adventurous, so we decided to go for it. We went to Target and bought the second cheapest hair cutting set they had. (The cheapest one, which Chuk tried to convince me to buy, was for African-American hair. Hair texture matters in these things, I think.) It cost $20 or $25, the cost of two haircuts with tip.
I was totally scared the first time I cut it. I had no idea what I was doing. I just followed the instructions that came with the kit. It was not hard, but I went slowly because of my nerves. The cut turned out fine.
I've been cutting his hair for probably the last six months or so now. It takes me about 15 minutes start to finish, including his inspection of my work and sweeping. It's certainly faster than the walk-in places and they're pretty much free hair cuts at this point, which we appreciate too. The set has a five year warranty, so if we figure that the set will last for five years and I give him one haircut a month, each haircut is about $0.50 each. Not bad.
If you've thought about cutting your guy's hair, I say go for it. Seriously, it's easier than you think, and much easier than using scissors. If you follow the instructions and go slowly, you won't screw it up. I promise.