The question isn't "will this ever work?", the question is (while keeping with your airplane analogy) is Elon Musk's design closer to the Wright brothers airplane or Da Vinci's ornithopter. I'd guess the latter personally.
The main thing Musk has in common with the Wrights is running an electric car transportation company and sending private rockets into space via SpaceX.
I think you should revisit whether that makes it more Wright brothers or Da Vinci.
You’ve found a flaw, I think a pedantic one, in the example they gave.
Here’s an example that is less flawed, and I think if you had considered their point rather than sought minute flaws you could see this yourself: the palm note vs the iPhone. Hopefully, even if my analogy is not literally flawless, you can take my point.
Also, sorry for spamming you, something you wrote struck me and I wanted to see what else you wrote. Hope you don’t mind this.