You say "some files", are we talking tens of files in a handful directories or tens of thousands files spread all over the place? Not sure if it solves the issue, and depending on the situation it may for a number of reasons not be manageable, but perhaps building a set of symbolic links with the desired extension in a separate directory could solve this. LMS scans a directory with one extension, iTunes sees another but it's the same file. To me, it seems better to never rename the files and let iTunes work with a bunch of symlinks, but if that doesn't work, try the other way around.
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