Nic, I know what you mean, and for my own photography I prefer to just stumble upon something that I find wonderful, and show my wonder in a photograph. I think most of us here are like that, and it's a type of photography that leans heavily on having the eye, compositional skill, timing and sometimes stealth necessary to translate your vision into an image. This guy's photography starts out with a concept, and then relies on creativity to turn that concept or emotion into an image. The cleverness usually isn't in the photographic skill, but in the concept first, and secondly in the way the concept has been brought to life. Once you accept that, I think it's a lot easier for us who love photography not only for the resulting images but also as an activity and a skill to practice, to appreciate the works of artists like Kyle Thompson.
From his shots, I prefer the shots that didn't require photoshop to make the concept work (for instance, I prefer the balloons/suit shot over the cloth wings shot), and in general I prefer scenes that, although unlikely and dreamlike, you could in principle find in real life without having to break any laws of nature. I feel the same way about surrealist paintings; I much prefer Magritte over Dali, for instance.