I was thinking about this while driving recently - both the iTunes &#x2F; Apple Music approach, and the way I go about organizing and sorting my things.<p>As a guy who grew up with Mac until playing catch-up with Win95 (and some DOS to fit in), being familiar with digital storage techniques has formed over time. I get the concept of certain files being certain places - system files versus personal files versus program resources. This kind of structuring appeals to me.<p>Thus, rather than totally embrace the &quot;OS as Helper&quot; technique that Windows likes (put everything in &quot;Music&quot;) or going the iTunes route (behemoth management program with hooks to other stuff), I maintained some of my fencing habits. Sure, I use the &quot;Music&quot; folder but that&#x27;s only for purchased music. In a separate folder - which makes things easier to back-up I think - I have my &quot;Music Projects&quot; folder.<p>In my workflow I&#x27;ve got my DAW projects and output separate from what I&#x27;d consider the &#x27;commercial music&#x27; area, and this might have saved a lot of stress that Pinkstone went through. Maybe not, but my hunch is it might have helped. iTunes can&#x27;t touch what it can&#x27;t see, and letting it anywhere near a collection of bootlegs and&#x2F;or &quot;less than legal&quot; origin files is something I would avoid out of general suspiciousness. That applies to original works that don&#x27;t fit any standard cataloging function either; I don&#x27;t think that would help me.<p>Personally I&#x27;m still satisfied with Winamp, a couple skins and visualization things (it does help me ID3 tag my music as well), and honestly can&#x27;t recall if I&#x27;ve ever installed iTunes in the past 10 years. I genuinely don&#x27;t think so, and while my own process has flaws and issues (overlap of versions, DAW files are big, etc) there&#x27;s some protection I kind of like in a way.