Yeah sorry I feel kinda bad about posting it. I can delete the comment if you want.
With this great effort and research though, wouldn't you have a mechanism in mind that would prevent this misuse?
For fonts the open source license equivalent is SIL Open Font License (OFL), which has a clause which prevents the "reuse" of the "Reserved Font Name". If we would translate this to Wigglypaint it would mean none of these sites are allowed to use the "wigglypaint" name in their brand. These includes many applications you documented. Technically this is probably already the case in some countries, but I think it is not explicitly stated in the MIT license.
Another license BSD-3 for example has a clause to provide some protection:
> 3. Neither the name of the copyright holder nor the names of its contributors may be used to endorse or promote products derived from this software without specific prior written permission.