It's a really good idea to invest in headphones that have a detachable cable, if you are rough with them at all(basically any travel or commute situation). Then the point of failure becomes the internal connection, which mostly rests on build quality and how much you drop it.
Have you ever seen any earphones (IEMs) with detachable cables? I could see them being produced with short cables to the Y split and then plugging in another cable to the phone.
This would be perfect for me - headphone cables and wheelchair wheels do not mix.