I had a kid a few years ago when I switched. Wearing headphones and holding a child sucks because they will probably get pulled out of your ears. I always hated cords tangling in my pocket and I'd often have the wires snag on a doorknob or drawer when walking around--often breaking them. I also used a messenger bag.

Ear fit sucks, is it worse with cordless headphones? Ear fit always comes up with earbuds, wireless or wired. I've heard individuals say wireless is better for them because there's no wire tugging on their ear. I'm surprised to see a lot of people walking around with over-the-ear headphones (I tend to use them at home or on a plane).