I agree with others here about iTunes. It's a bulky, ugly thing that in fact sits as an obfuscation layer between you and your stored music files. I prefer to go directly to the folder holding my music, and select the songs directly, or by right clicking the album folder and selecting Play with WinAmp. I avoid iTunes like the plague.
I have had WinAmp as my primary music player program on all the Windows machines in this household since at least 2001. I am listening to streaming music on it right this second, in fact.
I DO hope that WinAmp can split off from AOL and stage a kind of come back, return to the flexibility they used to have in choosing their destiny, even if they DID miss the greatest opportunity imaginable, and not by their own fault.