I have always been super-anal about file-structure & organization. I loathed big-bucket directories. I would carefully arrange applications into categorical subfolders, my documents were all organized by project in subfolders. My music has always been organized by letter->artist->album, with the large folders of letters being further sub organized. The idea was that I would never be looking at any folder list with more than around 30-40 items. Not sure how or why this happened. Likely years and years of working in DOS with tiny monitors and hating having to paginate listings.
But I realized lately that I essentially *never* browse my filesystems anymore. If I’m looking for something, I search. And I don’t care where it, because the spotlight search is so fast & efficient. We have historically had a pretty strict file-structure for web files too – for software packages, this is still useful. But we used to do it for assets as well – but now more and more we’re rsyncing uploaded files to big-bucket CDN/cloud servers anyway, so our precious file-system organization is not useful. And because there’s often a software layer between where files are stored and browsing them, we can use software to categorize the display in a vastly more useful manner than folders – this is the glory of tagging & meta-data.
And so, after my external HDD died at home, along with it my home music library, when I started to rebuild my iTunes library, I did something that would be anathema to me just years ago – I’ve let iTunes organize the files internally, however you like. & have set up watch folders for it to auto-import as I download from eMusic and whatnot. And it is very liberating. I haven’t pulled the trigger on it yet, but I might just do that for photos too, getting away from the year/month/day/file structure I’ve been keeping since 1996.
The future is scary and cool.