Graymatter,
I know I'm answering a bit late, but have you found a solution that you like yet?
I've gone through numerous models of IEMs over the years. So far I have found things that either sound good, or stay in my ears, or are comfortable for extended periods, but nothing that does all three.
Currently, I'm using Etymotic HF-3s. For daily use, the HF-3s have great sound isolation and very accurate sound. They are quite adequate for me, for everything except riding. Unfortunately, their lack of bass emphasis means a deficit of bass inside a full face helmet when at speed.
The other issue is comfort. I am currently using the included foam tips because the three flange tips become painful after a couple of hours or so. The foam tips result in slightly poorer isolation and sound quality. Plus they fall out more easily than the three-flange tips once my helmet is on. But I've had to make the compromise for long rides.
As I'm sure you've experienced, once at speed, bass disappears even with a good isolation seal. I really want better bass at highway speed. I'm not a bass head. I know it will be too much bass once I get off the bike. But I'm looking for a set specifically for long rides.
So, I have been looking for a small, comfortable, IEM with good isolation and bass emphasis.
I'm going to try:
Klipsch s4i
Scosche IEM856MD
I suspect that each of those two might be physically too large and either hurt or get pulled out of my ears once I have my helmet on.
But, both are apparently bass emphasized and have iPhone compatible controls. I'm not interested in talking on the phone while riding. But I require pause and volume control buttons on the IEMs since iPhone touch screens don't work with any of my riding gloves.
Any thoughts about those two? Or do you have any other suggestions?
I'm also interested in the Bose QC20 noise canceling IEMs. There is a great motorcycle specific review of them at webbikeworld:
http://www.webbikeworld.com/r5/bose-quiet-comfort-20-review/
They're very expensive, but I think they may be worth a try. If the "awareness" switch works as advertised they'd be an improvement over simple hearing protection (ear plugs) which I use even when I'm not listening to music. I'm skeptical, but they are returnable.
BTW, for all you safety dudes out there: every riding safety instructor and ultra-distance rider that I've ever met (myself included) will tell you that hearing protection is *required* at anything over 35 mph or you *will* induce hearing loss over time. The best hearing protection advertises about -30dB. In practice, reduction is really more like -25dB or less, which just isn't enough to prevent a rider from hearing a car horn, a siren or screeching tires. You listen to music in your car going down the highway, don't you?
I'm not a 15 year old kid riding a scooter around in city traffic. So, if you're a non-rider or a safety-dude, please spare us all the lecture.
Anyway, I plan on trying all three, but I'm open to any other suggestions.
Buy, ride, return. Buy, ride, return. Buy, ride, smile.