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It helps that my library is spread across several different fandoms and I tend to get super focused when I find something new I like, then gradually taper off and move to a new subject. I have a whole bunch of subfolders, so even the biggest one has only a bit over 100 fics. I can also easily identify series just from the .doc filetype.
It does take some guessing and blurb checking to find a specific fic outside my memorized favorites, but so far it's not very difficult. That might change as my library grows, but it's going to be a while yet. Also, when I get too many fics on my ereader I aggressively prune the ones that I kept "just in case" but honestly will never reread. My library on PC is over 3 000 files including copies of stuff I've deleted off the device but still want to keep. :P
You have a really good point about backups. That's definitely something I'll have to look into. I already backup my device regularly so it would be easy enough to add that to the routine if it's at all possible.
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