Well, you've hit on a few of the important factors regarding Bobby Quinn Rice's hairstyle:
1. Peter Kirk's hair only seems out of place and "non-reg" in a 20th or 21st century military service outfit; we really don't know what hair styles will be acceptable in a 23rd century Starfleet. How did you find out what the regulations will be 200 years from now to be able to determine that Peter's is "non-reg?" (Example: When I look at 18th and 19th century naval hairstyles, they are pretty long.)
2. If you give Peter shorter hair, the hairstyle begins to look military instead of pseudo-military. (The term Roddenberry used was actually "semimilitary.") So, we need to find ways to reinforce the "semi-" part and not the "military" part. Hair that would be inappropriate for the 20th or 21st centuries might therefore be the exact kind of thing you would want to rely on to convey that the organization merely a "futuristic" semi-military organization.
3. Janice Rand's crazy basketweave beehive is also out of place in a pseudo-military service outfit but most people don't complain about that (although a few do).
4. Walter Koenig had to wear a wig for his first few episodes while his "non-reg" longer Beatle-style hair grew in. So, the "new young character that kids can relate to" whether he's in 1967 or 2007, always needs to have an appropriate hairstyle so that, well, the kids can relate to him.
5. When we changed our moniker from "New Voyages" to "Phase II," we decided to adopt many of the art designs from the ill-fated 1970s Phase II series. This includes the costumes, some props, some sets (if and when we get to them) and, yes, even the 1970s hairstyles. Peter Kirk's hair faithfully recreates hairstyles seen on the men in screentest footage shot for the original Phase II series. The hairstyles will be one of the ways we try to "recreate" the Phase II series instead of just recreating TOS. So Bobby has Phase II '70s hair instead of '60's TOS hair. It's a shorthand way of conveying that this isn't exactly your father's TOS Star Trek. (We gave Scotty a "non-reg" moustache, too.) If it pulls you out of the same ol' TOS Trek universe, excellent. That's part of the point. As for "not bothering" to get his hair cut: you assume too much. In real life, Bobby does not keep his hair this long and he grows it out at our instruction. I'm sorry if our creative decision doesn't work for you.
6. Peter's heart isn't really in Starfleet in many ways and we need a quick way of showing that rather than saying that in dialog. He's ambivalent about being there and, as we've seen, he came on board the Enterprise mostly to be with Lt. Alex Freeman. Giving Peter longish hair is an intentional way of showing that he's not really toeing the Starfleet line.
7. After five episodes with Peter's long hair, I believe we'll find that it's no longer really working for Peter--and as he grows up and he finally takes his position and responsibilities in Starfleet more seriously, he'll be adopting a more "appropriate" hairstyle to convey that he's really, finally joined the team. So, shortening his hair is something we'll probably rely on in our next episodes.
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