Is he failing?
At what? Look at his employee turnover. Does he suck at hiring, or is he atrocious at retention? Maybe both, but one has to be true.
Does he have good people working with him, including military experts?
Fewer every week, seemingly. Replaced by toadies that he "trusts" because they soft-pedal his ego.
If he is screwing up, thats one thing but it appears he is doing a pretty good job.
Because as best I can tell, your philosophy is that breaking government equals "doing a good job" because that means it gets out of the way. That's cool and all, and there are, believe it or not, some cases where I would agree with you. That's all fine and good and fun when we shoot the bull about taxes, political correctness and the government's role in directing social policy. It's a little less fine when you need expert-level coordinated response for an honest-to-God emergency.
Does he have good people working with him, including military experts? Is he an expert in supply chain management or has he got the best guy he can find doing? I would submit that Kushner is doing exactly what you have done, finding someone better than him for a specfic task, listening, and managing the process. Question, why would you have a problem with friends or family if they were up to the task and you trusted them? I would venture thats exactly WHY Trump has chosed both...more for trust than any other reason, and the outsiders have given him good reason not to trust them.
This is the great unknown, right? As I said, to this point, whatever our disagreement may be on policy, it's undeniable that Trump has either done a poor job recruiting talent, or a poor job retaining talent because of his ego. Both are signs of a poor manager. This has been the crux of my issues with Trump from the start. I mean, sure, his social policy is retrograde, reactionary, and plays to the lowest common denominator, but fundamentally he is just a piss-poor manager of people and bad at looking at divergent points view. He thinks he already knows everything. And that's a bad guy to have in charge of the world's biggest organization, where literal lives depend on his competency. Does it even matter? Almost everyone that leaves the administration claims that he doesn't listen, doesn't learn, and has no interest in information that disputes his preconceived notions, and those that don't say that are still angling for, or part of, the entourage. I'll be pleasantly surprised if he rises above that now.
So your managment style differs from Trumps. Ok, no problem. Despite what some my think, the last three years look pretty good from my seat...we will see in short order about the virus thing.
Good luck to us.