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I used an iPhone to listen to music, no problems, just don't crank up the volume. If you can hear the rest of the world then you will be ok.
My experience of bikes was even with or without the music you missed some and 99% of the riders were cool.
For me walking is in itself meditation...
Just walked in May, didn't get any problems personally but did meet those who had. They were in the minority not majority.
Used a silk sleeping bag liner, which was from Lifesystems and came already treated. The liner was good, sometimes a bit too warm, but worked.
Don't worry too much about bed...
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