With me it's always the same story, I wear them pretty much every day and after a certain period, I wake up to them only playing in one ear. I've tried really nice and expensive ones, I've tried lots of cheap ones; nothing works. The seem to last a proportionate amount of time to how much they cost, but they all go out. Can anyone recommend a pair that will last, and are comfortable? Preferably available at a retailer like best buy but if not I'll work it out. Thanks.
Are you taking them out by pulling on the cable? Over time this will break the cable and hence why one ear would stop working. I have had a pair of Bose earbuds for about 4 years, not sure of model but they are as good today as they were new. I am however very careful with them and always put them back in there case when not in use
Perhaps look into an iem with detachable cables. The Shure Se-215 is a good option for $100. The only problem is that the stock cable is not very flexible but if you can get around that the build is solid. They come with a few pairs of foam and silicone eartips so it shouldn't be difficult to find a good fit. For extra comfort you could look into memory foam eartips like Complys.