Hi C.!
Have you thought about *not* cutting his hair? It may not be *your* desired solution to the issue, but it sounds like *he* is telling you something! When I had dd, my first child, she always wanted her hair cut. But I just couldn't bring myself to do it. I don't know why, it just felt so....wrong to me. She didn't want her hair brushed, braided, barretted, anything! She doesn't even particularly like to wear hats. From a very early age, she has told me she just needs to "feel free," that she "loves to feel the wind in her hair." With ds, he was the opposite. He wanted long hair. Even when it was in his eyes, he didn't care. I didn't want to make the same mistake twice by not listening to what my children were telling me...of course, his mama and daddy both had long hair at the time, so I think that was part of it as well. On the day daddy decided to shave his head, ds *and* dd decided they wanted to shave their heads, too. So they all did. Dd is feeling good because her hair doesn't need to be brushed or braided, and ds is feeling good because it was *his* decision when to cut his hair.
I think one of two things may happen...either your son will have long hair, and like it, or eventually he will *ask* to have his hair cut, in which case, he will like it, because he asked for it. Either way, *he* will be happy, and *you* won't feel like you are battling him or having to break out the punishment/reward system to get him to do something he clearly isn't comfortable with.
I think some people are cautious to let their little boys grow their hair long because people might think they are a girl. I can't tell you how many times people thought my dd was a boy (even as a baby), and my ds was a girl (as a baby as well), and regardelss of their hair. So what. Only your child can decide if that will bother him or not. My dd has been called a boy several times since she shaved her head. Some of our friends even call her her brother's name because now they look so much alike. But she likes the way she looks and feels, she isn't bothered by it, and feels really good about making the choice for herself. Her independence and autonomy are *really* important to her (both of my kids are this way), and it is important to me to honor that, and help keep that part of them as intact as possible.
By honoring my children's choices, I feel that they trust me to really listen to what their thoughts, feelings, wants and needs are, and to help them achieve whatever it is they are setting out to do. Just remember to remain open to *all* the possibilities, even the ones that might trigger some 'negative' emotions for you. Oh, and you just might want to ask your son if he wants to have his hair cut. If he says 'no', you could ask what he doesn't like about having his hair cut. I would also recommend trying to figure out why it is so important to *you* to have *his* hair cut. And whether the battles are worth it or not.
Love and light....