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 _rsync_ing 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.