First off, I'd like to say that I am by no means an expert in the subject. I major in Engineering Physics and have taken a 2nd year university course in optics as well as a 4th year level course. I have learned a few things so all I can offer is my scientific explanation.
First thing to understand are the coefficients in between reflection and transmittance. The coefficient of reflection and transmittance are related through stoke's relation http ://en.wikipedia.org/wiki/Stokes_relations.
Think of the fiber optic like a cavity. The principles suggest that light will enter and get "trapped" by being continuing bounced off the inside. http ://en.wikipedia.org/wiki/Optical_cavity . Although the fiber optic doesn't use the same optical cavities that are required for lasing, it still gathers light. By trapping light, I mean that light will be repeatedly bounce off the inside edges. What happens if light comes at any angle? Eventually, a good portion of that light will reach the ends.
I think the mistake is thinking of the fiber like an optical waveguide. Any light that enters into the rod from one end will propagate until it reaches the end. In addition to that, light can still enter from the sides. Your misunderstanding comes from the part where you have deduced that light has to come from "inside" the medium. It does not. You have already deemed that it is impossible for that scenario to occur for the picture with the critical angle and the beam thats "impossible". The critical angle is not important in whether or not this works. It tells you which are the allowable angles for total internal reflection to occur. Light can enter through the ends and propagate to the other end but this does not explain why it's BRIGHTER.
If you point your sight at something bright, it won't appear brighter. Let the light source shine on the sides and you'll see it very bright. Also try this. Cover up the front of the sight and you'll notice that as long as you let light hit the sides, the sights will still appear just as bright.
I am also a little confused why you need it to "channel light in one direction". Light will exit on both ends of the optic fiber. And this is mainly due to the fact that "less light" exits through the sides than enters through the sides.
I'm not sure if I answered your question but I don't really understand what you mean by
only a less optically dense material on the outside and air is almost the best thing
. Do you mean that a light in a material that is optically more denser than air?. Also, In fiber optics, the critical angle is not the angle at which they transmit. They do not want the optic to travel parallel in the direction of the material.
Tell me what you think. It's really late so I don't know if I have made my points clearly.