FYI, there are a few active items on the bug tracker related to some of the IDLE dialogs, if anyone wants to chime in on some potential changes:
http://bugs.python.org/issue24776 <http://bugs.python.org/issue24776> Improve Fonts/Tabs UX for IDLE http://bugs.python.org/issue23218 <http://bugs.python.org/issue23218> Modernize the IDLE Find/Replace/Find in Files dialogs http://bugs.python.org/issue24781 <http://bugs.python.org/issue24781> Improve UX of IDLE Highlighting configuration tab http://bugs.python.org/issue24782 <http://bugs.python.org/issue24782> Merge 'configure extensions' into main IDLE config dialog http://bugs.python.org/issue24760 <http://bugs.python.org/issue24760> IDLE settings dialog shouldn't be modal
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