I'm very wary of the MSM (new motto, All the skews we see fit to print.), but it sounds like Kanye has fallen into the trap of, "Hitler did good for the German economy," while ignoring the 5 or 6 million Jews he slaughtered, plus gypsies, plus homosexuals, plus the disabled and mentally ill, and the 10s of millions who died in the European war he started. Flipping the old analogy, it's like Kanye (and the many others before him who said similarly) says, "Look! There's a chunk of brownie somewhere in that truck load of crap! Let's eat!"
As for Musk and Maher, when they say something good, they said something good and that's all. They aren't particularly near the realm of principled conservatism.