First, thanks to the many who have previously weighed in on previous threads about best IEMs for sleeping. Many point to the MEElec M6s, the Soundmagic PL50s, and Westones, with somewhat less frequent nods to the q-jays, db-Logic EP-100s, Shure 215s, and Phonaks.
I too am looking for recommendations, but with an additional concern in mind that I have not seen mentioned in the previous threads: Even if I find an IEM that is comfortable enough to drift into oblivion with, I find that in order to avoid severely dampening the sound of the downward facing channel, I must either make an elaborate pillow mountain range and place my ear in a valley or try to arrange a pillow such that only the portion of my skull above the ear is bearing the (obviously not very large) weight of my cranium. Doing this has made me increasingly less popular with my wife and frequently results in a stiff neck, but I often need music to fall asleep.
I think I know that dynamic drivers are all either side or rear vented, and I'm guessing that this is why I have the issue: my ear is pressed against the pillow and there isn't enough volume of air (or there is enough of a vacuum) which affects the sound. Are BAs sealed and immune to this issue? Any techies out there who want to weigh in?
Maybe you side sleepers who have had success with dynamics want to weigh in?