The question how to rig characters with outlines has popped up multiple times.
In the world of digital cutouts outlines make life more difficult and complicate everything. This is why a large part of the character designs (and rigs) don't have any outlines at all, or only have partial in the facial area, hands, feet and some wrinkles here and there.
Ultimately, it is an artistic and stylistic choice. Read more
I’m finally using your Flash Power Tools, and they’re fantastic. Just one suggestion – put a “donate” button on your site! Or a Flattr button, or something. I like to support Free software, even if it’s with just a few bucks.