Can a software license restrict copyright of (non-derivative) works created with that software?

Question

MacroHard, a US-based corporation, creates a software, Acrylic, to make pictures/diagrams. The software allows to draw some basic forms (rectangles, circles, stars etc.). If it matters, suppose the software is downloadable from the internet at no cost.

Bob, a US-based professional designer, wants to use Acrylic for his work. He reads the Acrylic’s EULA and reads:

You may use pictures created by this software in educational materials, websites, presentations, social media sites, and for internal communication. However, you may not share or distribute such pictures in any way that would let others use them without licensing it themselves and you may not use them in any publications, marketing materials, or for any commercial uses.

Bob understands that the license terms purports to restrict copyright of the images he creates with it. As the software itself contains only simple shapes, he reasons that pictures created from it cannot be derivative works, and that therefore those terms are void. After all, MacroHard also provides a text editor, Sentence, and does not claim copyright on any text typed with it (formatting may be another matter). He therefore resolves to ignore that part of the license terms.

Can MacroHard’s (numerous, well-paid and aggressive) lawyers successfully sue Bob or Alice in the following scenarii? If yes, what kind of compensation can they seek?

1. Alice is the CEO of a company that produces widgets. She hires Bob to create an ad for her widgets. Bob designs a poster using Acrylic. The poster is printed and shown in the streets of their city (New York if it matters).
2. Same as 1, but Alice is Bob’s sister, and Bob does the job for free.
3. Alice is Bob’s sister, and a school teacher in the impoverished public education system. She finds the teaching materials insufficient, and asks Bob to create diagrams that she would show to her students; Bob creates those diagrams for free, using Acrylic.
4. Same as 3, but Alice is now a teacher at a (very expensive) private school.

The question Software content library license requires "including a valid copyright notice". How does it limit my use? is similar, but it involves a more permissive license and the software contains assets with a clear copyright claim.