Do you backup your files? Do you clean them up up from time to time?
Usually there’s a prompt. If I get a new computer, I look at the binaries I kept from the last one. Still need em? No? Trashed. If it’s taxes, organize by year, and you can pitch any folder older than seven or ten years. Receipts and other records can be sorted by year as well, and pitched with the taxes stuff. Any exceptions should be kept elsewhere for retention.
Other stuff, like documents from old jobs, I organize by gig or topic. A lot of it doesn’t matter much whether that’s dated, as it’s more memorabilia than important files I need for . As storage ever increases (locally or in the cloud), as long as you can find it, how much of it matters less. If you index it once, you can use disk search to find obscure stuff locally, but if it “piles up” a little, what’s the harm?
Music’s a funny one. Like my DVD collection, there’s almost no point in keeping any of it, even if I ripped my CDs in lossless. Streaming’s better quality now anyway for audio and video. It’s “outdated, but there are still a few things you can’t get anymore. Sorting those is not a task I’ll relish, but I’ve also not added anything to those files in years. Additionally, if I were to lose the music files, would I even notice? I can’t think of the last time I listened to files vs. just streamed content.
Pictures are organized by years. Rarely if ever do I lament keeping pictures, but not so if I’ve deleted some. They stay.