I don't ride clipless. I did for awhile on my road bike, but I decided over time that I just didn't care for it and didn't see any benefit, so I went back to regular shoes on flat pedals. I'm very happy riding free and wouldn't have it any other way.

I've discovered that I can get power to nearly all of my pedal stroke when riding free that doesn't involve mashing. It's just all about technique.

Regarding the iPod, I used mine a lot on the bike when I was riding on my slower hybrid. But when i switched to the road bike, I had to stop, because at higher speeds the wind whooshed in my headphones and it was too loud.