Hmm, perhaps it has to do with me having extremely small ears. Even before, when wearing them with stock tips, the tip of the strain relief would already be at the point where the cable starts to go over my ear, so the year and a half of use has taken its toll.
As for why I wear them over the ear, it's because I like my cables to disappear behind me. It could be due to the fact that I drum and I use these for monitoring, so if the cables were in front of me, they'd get in the way, so it's a habit that just translates even to normal, on-the-go listening. Cables behind also does mean reduced microphonics, comparing directly to if cables were in front and able to get in the way of just about everything.
A little pointless to say, but I do hope FS takes this into account - perhaps consider a shorter, neutral shaped strain-relief, like how Westone and Shure do it, so that it doesn't have to be curved under normal usage. I also own a pair of UM1s, and the strain relief is still quite fine. I belief that strain relief isn't meant to be strained on a regular basis (if it were, then there should be memory wire there, not strain relief). Its purpose is to protect against the cable severing itself from the driver housing in the event of a sudden strain or tug on the cable.