IPod 4G click wheel wont sync with itunes with firewire and USB

my iPod 4G click wheel 20GB won't sync with my Macbook Pro OSX Mountain Lion.......
only way work is .. I keep plug in and out the dock connector from the iPod ... after 30 to 50 times... it probably work!
Anyone has same problem?!

Do you have another cable you can try to rule out the possibility that the cable is damaged or faulty?
You might also want to double check the iPod's dock connector for signs of bent, damaged, or corroded pins or even debris that could blocking a full connection with the cable.
B-rock

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