The biggest problem people have with Hyperloop is because it certainly seems like Elon Musk just waltzed into the high speed rail debate and Dunning-Krugered some crazy scheme that doesn't look anything at all like conventional approaches to the problem and thus doesn't jive with any common sense we might have built up around different transport methods.

But that's kind of what Elon Musk does: he Dunning-Krugers himself into a new industry every couple of years, using a simplified, undergraduate physics level of analysis to find something that (to an optimistic non-field-expert) looks like a better solution to the problem.

And the most annoying thing of all is that he usually succeeds. Often in spite of his original idea being technically wrong. For instance, Falcon 9 was supposed to be recovered with parachutes... that didn't work, and people who were working on vertical landing rockets told them that, but at the time Elon just rolled his eyes and said "just use parachutes." But SpaceX/Elon found out the idea didn't work and switched to the "correct" solution and got it to work operationally (and with paying customers) much faster than people who had been working on the problem for years before.

The moral of the story is that it's often better to be able to execute fast even if you start out wrong than to take your time with the right answer.