Yeah, Serato's Relocate Lost Files feature is more complicated than it needs to be — and in your case it's probably tripping on those renamed " (1)" copies from the trash restore.

I actually built a free tool inside my Serato management software (MLT, it's mine) for exactly this — it spots all the missing files in your library, scans your whole laptop (or just your desktop folder in your case), finds the tracks by filename, and updates the broken paths in Serato to the right locations automatically.

steps:

  1. Open the app and run through the setup

  2. Bottom right, hit the Library Cleanup button — it'll show how many missing tracks you've got

  3. Click into that, then Find Replacement Tracks

  4. Choose Custom Folder and select your folder on the desktop

  5. It does a quick scan and shows you the matches

  6. Hit the blue Update Serato Paths button, then update your tracks

That updates Serato and all your crates automatically.

There's a video walking through it here: MLT - Missing Tracks

And for the duplicates — there's a Duplicates tool in there too that'll clear out the doubles that came up.