Three years ago I picked up a used copy of Frankenstein with like 400 pages of footnotes from the 1970s, and I only bought it because it was three dollars at a library sale. I figured I knew the story from every movie and pop culture reference, so the book would be a quick skim. Turns out the annotations were mostly about the Shelley family drama and who actually wrote what parts, and I got so caught up in the footnote about her step sister that I forgot I was reading a horror novel for like twenty minutes. By the end I was more interested in the real life people than the monster, and now I tell everyone the best way to read a classic is to ignore the main text and just follow the footnotes like a treasure map. It completely ruined the book for me in the best possible way, because now I can't separate the story from all the messy history around it.

That's the real question here, isn't it? Before you even think about sorting files, what's the actual plan for next year's taxes? Because if you don't have a simple way to grab receipts and forms as they come in, you'll be back in this mess by next February. Trying to fix 14,000 old files is one thing, but what's the one thing you know you'll need to find on April 14th? Start there, and build the whole system around that single file, not around categories that sound nice but mean nothing when you're in a hurry. The old files might be a lost cause, so focus on what's coming next, not what's buried.