Hi There,
Thanks for writing in!
I checked the Classic list item in mac Safari on my setup its working fine. I can able to edit the text. I am not sure exactly what happening in your end. As we don’t have access to your site, I would like you to check few trouble shooting process.
First please disable all Third party plugins and remove all custom JS if you have any in your site.
If that doesn’t help Please send us your login details so that we can have a look. Post the details in a secure note.
For the second point, I am not sure what exactly you want to achieve here please send us a screenshot or mockup so that we can suggest you better.
Thanks