More anecdotal evidence: I wear just one side of my headset. I mean, if I can't get a one-sided headset, I buy a 2-sided and literally cut off the right side so only my left ear is covered. In the past 10 years, I've gotten 2 infections in the ear that is covered and none in the one that is not. Take it for what it's worth.
When travelling in an aircraft I found that bone conduction headphones didn't work very well for me. There is too much external noise from the engines and ventilation system. It overwhelms the sound coming from the bone conduction headphones.
When I use earbuds on an aircraft it is amazing how loud they are. I notice this when I am no longer on the aircraft and use them without adjusting the volume first.
Noise cancelling headphones on an aircraft work very well for me. It is amazing how much noise they cancel out during the flight. I even notice while wearing them, I can even understand the flight attendants when they are speaking to me. This is generally if I am listening to a book, checking email or reading text. If I am listening to music it is more difficult to hear anything else, because of the wider range of sound.
Bone conduction headphones work nicely at work and around the house while I'm puttering. Even while outside I like them. If I am not in an area where there is a lot of traffic noise I like using them with a GPS solution. In noisier environments I find using an ear peace like the Jabra Supreme works well. It has noise cancelling and I find unlike an earbud it doesn't get sucked into my ear canal blocking out a lot of sound. In fact although it does alter my hearing somewhat while out and about, it is no worse than wearing a toque during the winter. I found it very easy to get used to and it also works nicely when I receive a call when I'm on the move. The closest items I found that work OK for me while outside are the earbuds Apple sends with their iPhones and other iDevices. The only thing I can surmise is that because they have a hard shell there is no soft rubber or foam to seal my ear canal.
I have resisted the temptation to use earbuds during the day at work. This is purely anecdotal, but a friend did tell me when he used to use earbuds the rate of ear infections for him seemed to increase. Using earbuds that didn't have foam coverings although easier to keep clean, didn't help. Moving to external headphones resolved his issues.
As for leaking, I noticed that the second generation of Bluetooth Aftershokz worked better. They have larger transducers, better sound and less leaks. I haven't used their latest offering yet.
Vic
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