Music pauses and needs double click at the remote to go on

I walk my dog 3 times a day, and I always do it whilst listening to music on my Iphone 3GS.
At the beggining I did not have this problem, but all of the sudden it started to happen.
The first time I play music once I'm on the street (specially if there was a restart before) it's fine, but if I manually pause the music with the clicker, after I unpause it begins to do random pauses in the music. It could take 5-20 seconds or even more than a minute to do so. And to unpause it, I have to click once, I hear music for about 0.2 sec, it gets paused again, and only with the second click it gets really unpaused.
After this happens 2 or 3 times in the same walk, the next unpause makes the music start to sound all cracked up and I have to disconnect the jack and put it back on. That solves it momentarily. If I pause manually again, it all re starts.
But the crazy thing compared to everyone else having issues with music randomly stopping, is that I always need to press the clicker twice to playback.
Note: I pause the music manually many times because I cross other people's dogs and I start chatting with them.
Music never skips, only pauses.
I have changed headphones without any luck.
I went from a 3.x firmware (don't remember which one I had) to 4.3.1 with the same results.
I have tried listening to music with no applications at all loaded into memory except the ipod.
Shake to shuffle is of course off.
I have tried another application to play the music with the same results (but I think these apps really use the ipod app to actually play music).
I have cleaned the jack with q-tips, air etc.
I'll aprreciate if anyone can shed some light to this problem.
Cheers!

Restore your iPhone and sync the music onto it again. Because it's jailbroken, there is no other way to isolate the problem.
Post if the issue persists after the iPhone has been restored.

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Music pauses and needs double click at the remote to go on

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