Yeah, I try to stay away from pills and such as much as possible, so I don't have a lot of experience with pill popping.
Recently, though, I was visiting a friend who has cats, and helped her move some furniture. Now, in general, cats are not a big problem for me, but when you mix that in with a bit of exertion, breathing becomes a major chore.
My friend offered some ibuprofen, which I figured should help somewhat, since it acts as an anti-inflammatory agent, so I decided to take it. I stared at the pill for a while trying to remember how I was going to do this without choking, and then finally just tossed it in my mouth and gulped it down without giving it much thought.
I think the main thing is just to swallow it without really thinking about it. You have a natural swallowing mechanism, but for some reason, pills can make you forget how to do it. So, my advice would be to stop overanalyzing it and just swallow.