I used to be kind of obsessive about my iTunes playcounts but that was when iTunes was the only music player I used. These days I'm listening to music on at least 3 different sources; my iPod (which goes towards iTunes plays of course), foobar2000 (with Windows) and Banshee (with Ubuntu), so I kind of just stopped caring about playcounts in music players. I am a little bit more obsessive about last.fm playcounts as all my plays go towards that and I can get a better idea of what I've listened to there. Yeah it is a pretty pointless obsession but it's always nice to keep track of what you listen to and to see your charts and stuff.
I've never really tried to get over it as such as it doesn't affect what I choose to listen to. I'm not going to listen to a certain artist or album just to increase it's playcount. I guess one way to try and get over it would be to listen to more physical formats such as CDs and vinyl, it'll help you to stop caring about iTunes plays or last.fm scrobbles etc.
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