Doesn't play music when docked

My iPhone 4 does not play music when docked on any type of docking station or when I plug it into my iTrip in my car. It still charges just fine, but immediately stops playing music when plugged in. When it is plugged into external speakers, it stops playing on its own speakers as well.
I also have an unrelated problem that came up yesterday: my phone's power button is jammed up. I cannot even push it anymore. This is my 3rd iPhone in less than a year that has had this problem. I don't think I push the button very hard at all, not anymore than anyone else. What makes this happen, and can I get it fixed without paying out the *** and without taking it apart myself? I got my phone from Best Buy as I don't have an Apple store within 150 miles of me. I am currently using AssistiveTouch instead, which is just plain annoying. Please help with either problem if you can!

Recently, I have the same problem but with my B&W Zeppelin, and it turned out it was the problem of B&W and has sent it for service.

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