Oh, what a conundrum. I, also, have problems with the reduction in value of files. One of the reasons I refuse to use Apple’s Mac OS is its difficulty in working with files. Having started from the beginning of the personal computer age I spent years organizing files in directories and ensuring redundancy with backups. Renaming files to better organize the archives was not fun but a very satisfying process that kept me in touch with a vast amount of data.
As a CIO for college over the last seven years I can go back through my directories that were all moved to OneDrive with archived work before that kept in small, early USB drives. Those live in the bottom drawer of my desk. I admire them occasionally but have realized that they contain things, several companies that no longer exist, that are nearly archeological. Geological?
I don’t look and can’t imagine when I would. That is to be expected for things like that. The company assets were sold and have gone on in other forms while I don’t find those things useful as nostalgia.
But my point is that all of my organized annual and permanent directories with my files were large and divers six years ago but have shrunk year by year into one for each year. What were numerous subdirectories have become, as you note, just thrown into a pile.
I’m embarrassed to look at my OneDrive. And I, too, keep everything in my Office 365 Outlook email. I would never admit that except that I just did.
I was corrupted by iOS, Sam Sung, and Android. Everything is just a message or an attachment or else stored by an app in its cloud.
Data is diverse and dispersed that search is the only way. Since I run all virtualized desktops with cloud storage I’m very nearly fileless. Have I lost something important? Probably but it is too much trouble to look for it.