Thanks again for the reply,
For your first question, I moved the two Knights & Woodland Hunter next to Company Supplier then gave up that strategy thinking I needed to do something else first to trigger progress.
For your second question, after doing what you said and making Company Supplier and Syndicate Descendant talk it did advance to Level 3.
That hint of making Company Supplier and Syndicate Descendant talk helped tremendously. It all clicked in my mind. I realized what I needed to do for all the characters and I ended up beating the game tonight, finishing the main story, and seeing all the current content . Great and charming game.
Also for the Syndicate Descendant Level 4 event, something happens to her face sprite with it doubling.