The problem looks like it stems from the way Tk::FileSelect handles file masks, and its selection verifying feature. You aren't allowed (by default) to pick directories, just files. So when you select /usr/local/*, you're seeing odd results because you're not selecting the directory itself, but all of the files within it.
If you add $fs->configure( -verify => [ '-e' ] );
after you create your selection dialog, it will switch the verification flag from '!-d' (don't select directories) to '-e' (select anything that exists). My test program returns just the directory name when that line is inserted.
For more info, check the CPAN docs for Tk::FileSelect
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