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SE215's also work quite well for sleeping with.
Raguvian, thanks, I looked into them and these looked great at first BUT:
I don't want to wrap anything around my ears.
It seems there is a design flow that causes the sound to completely cut out, which will be bad, because I might not even know that, being asleep or half asleep...
The removable cord design sounds great but in my situation, sleeping and turning -- it might completely detach.
Here's a review from Amazon that mentions some of it:
Just got these earbuds last week. I am a weekend musician and planned on using them for both in-ear monitoring on stage, and mp3 player use on airplanes, etc.
After one use in each application, I am very happy with the sound, and VERY unhappy with the fact that every time the cord moves, sound cuts out to one of the earbuds. Where the removable cord attaches to the earbud, there is a design flaw that permits cutting out. Trust me, nothing is more frustrating than being on stage and having to stand still like a robot in order to be able to hear out of both sides of these earbuds.
I returned them immediately, and am very disappointed in Shure. This should not be happening on the scale that it is. Google search SE215 problems and you will see what I mean. VERY DISAPPOINTING.
I can sleep on my side with M6,IE7, IE8, UE700, UE600, SM3, RE0, CK10, two reshells and a custom, but the not the SE215. They are fine on my right side, but on my left, the sound tube angle doesn't fit so well with my ear and it pushes into the side of the canal and blocks 75% of the sound.
I don't really know about the Shure SE215 but my SE425 has none of those problems. I slept with it no problem (no blocking whatsoever).
I don't know about under $50, but UE700's are the most comfortable "bed" IEMs I've ever used. Even more comfortable than customs.
My goodness, you have at least 8 IEMs?