You saying over time and usage, so was yours fine when you first got it. I wonder if you have a particular headset that is a little large and stretching the contacts. I've used mine with a headphone all the time at work, in my truck on longer drives, etc. My microUSB port is actually getting a little loose from being plugged and unplugged so much but the headset jack is fine.
I ripped one of my CD's to flac and through my cheap headphones I can't tell a difference between that and mp3. I need to steal my flash drive back from my son and see if my nice system will even play flac.
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Motorola Droid running Froyo 2.2 FRG01 by Pete
Asus eeePC 900HA, Seagate 500G Drive, 2G RAM running Slackware 13
Dell Latitude D620, 160G Drive, 2G RAM running Vmware ESX 3.5
Dell Latitude C400, 40G Drive, 640M ram, Atheros 802.11a/b/g wireless running BackTrack 4
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