I have had three iPods as I mentioned here. At the beginning I used some older Sony headphones and then later I used the ER6i ones I mention here. The only problem with the ER6i for me is that my first pair started having issues with the left headphone and then eventually both stopped working. I bought a second pair since I liked them so much and they have also broken. The second pair was under warranty so I sent them in for repair (replacement). In the meantime I have had to use the Apple provided headphones, particularly the ones that shipped with the 3rd gen nano. These headphones are HORRIBLE. They don't fit my ear at all so as a result they both fall out and hurt my ears. Secondly they have no sound isolation at all so you have to turn them up much louder than you should need to. I can't wait to stop using them and go back to a decent pair of headphones. I will say one thing in the headphones defense is that they are thrown in basically for free with iPods that sometimes cost less than the headphones I use. Still they are BAD, VERY BAD.
Apple recently released iTunes 7.5 and the 1.03 firmware for the 3rd gen nano. I am not sure which fixed this problem so I mention both. My previous Minis would sync and then prepare for disconnect and only draw power from the USB. The nano on the other hand would sync and they stay connected, thus forcing you to have to press eject in iTunes to allow you to properly remove the device. The only downside to these upgrades was that they essentially reset my iPod and all of its previous settings. I had to go back in and configure the music, podcasts and pictures tabs. I also didn't get my status of podcasts synched back to itunes and had to manually update which ones I had listened to. Hopefully a one time occurrence but still annoyance.
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