Using Windows XP I too have had issues with rescan failing on extra-long song filenames in extra long foldernames. The easy way to tell if a song has too long a filename is to right-click the song (the WAV or FLAC or MP3 file) in Windows Explorer. If the a shortened popup menu appears (no rename option) then the filename is too long. Move the offending folder and retry the rescan. Another issue I had with rescan was the use of an invalid character (a greek character) in a song filename. I found that one the hard way. I emptied my music folder, then rescanned. Worked okay. Then moved the first ten albums back into the music folder, and rescanned. Worked okay. Repeat until the rescan fails. Then you know the bad song is in one of the last ten albums, which you can manually browse, looking for problem filenames. That is, looking for filenames with weird characters or too many characters. Hope this helps.
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