So basically I think we have the same kind of hair, similiar color, straight, and it looks like mine does when it gets longer.
I used to keep it longer (similiar to how long you have it now, but brushed to one side) and hated and agonized over it. FOR YEARS. It was awful.
Finally one day I managed to get up the confidence while I was at a barber to get them to trim it way back. Actually, I kind of felt like an idiot because I sort of had them cut it the way it used to be THEN decided I wanted it cut way back)
Anyway, I am much happier with mine now. I go in and say, "Trim the top with a 4 and the sides with a 3." (those are the numbers of the little widgets that fit on a pair of hair trimmers, any barber knows what you mean)
It is a short haircut, but doesn't look too militant or anything. I take a shower and it is good to go. No gel, sprays or crap. It doesn't look like some cool ass model haircut, but that isn't me. It certainly doesn't look like I am trying too hard either. It is one of those things that you won't really know if you like it till you try it and see it on yourself. The first time I did it was when I knew I could get away wearing a hat for awhile if I hated it. It turned out better than I expected.
I won't get into the whole rating of you thing because I have no idea. But you're not a bad looking guy. My only regret is not cutting my hair short when I was way younger. I am much less worried about it now. If I were you I'd try some different things until you find something you like.
Oh, and again, I have no idea, but I bet that if you went with the short hair a short beard or goatee would look OK on you. Don't know if you can pull it off yet or not. A stringy teenage beard isn't a good look on anybody, but you might keep it in the back of your mind for someday.
Good Luck.
Edit: OK, this is totally not a real pict of me. That will never happen, but this sort of looks like what I am talking about:
http://images.google.com/imgres?img...rcut&start=18&ndsp=18&svnum=10&hl=en&lr=&sa=N