Every single example you give either falls under contractor or employee. Simply because you don‘t know legal language, doesn‘t mean lawyers don’t have simple, binary ways to deal with this that fully captures all of your examples. Law is not at all wishy washy in this case. If both employees and contractors are captured, then you‘re literally covered.

What I do agree with, is that any careful corporate lawyer would have a good look at this license and check whether there are any courts that have ever looked at this license to see how battle tested it is. Speaking as a lawyer, what I would see as an edge case that might be problematic is if a competitor of Outline that uses its completely self-built tech stack to provide a competing service as outlined in that clause would use Outline internally as a knowledge base. But I mean that‘d be absurd.

// addendum Personally, I think it would be cool if Outline at some point removed that clause, once it has built sufficient moat around its commodity services.