I’ve been through a number and to be honest found any device that relied on ear buds and a perfect seal inside your ear was worse than useless. Worse than useless because now I had a whole new distraction to stop and fiddle with as the music drops in and out constantly.
I’ve been doing some underwater + headphones stuff at work. Once you get the hang of putting the headphones in your ears and possibly get ones that are the right size and shape for your ears, they can work okay. But I’d agree that they are a pain to set up, and a fiddle, particularly when you first get them, and if I was in the market for an mp3 player only, I’d get something that did bone conduction. Sound quality underwater is pretty much going to be rubbish whatever you get, and it is surprising how much noise swimming even quite slow and smooth crawl makes.
But personally I think the whole experience of swimming with music is not that nice, I feel that it’s better to get interested in the swimming by doing productive training things like intervals, messing with pacing, doing drills, rather than using music to avoid having to think about swimming and becoming a pool robot or whatever you like to call it. It’s all about technique and feel for the water after all not just fitness, and not paying attention to your technique is surely going to lead to bad habits unless you’re already perfect, or at best no real improvement?
I think if your swimming is so monotonous that you need music to do it, then you’re probably not training right. I’m pretty sure I couldn’t do the kind of 2-3km training sets we do at our club on Sunday nights with music – on a good set I don’t have any spare concentration to listen to music with. Even training for an actual long event, like a 10k, I’d be mixing things up during training rather than resorting to mp3 players (although maybe I’ll think differently after June’s planned 14km swim!)
