"This is why the hated Trump is so beloved, notice how the
  campaign slogan isn’t ‘Make America Greater’, it is ‘Make
  American Great Again’. This admission of a failure is
  fascinating (for a politician) and utterly ignored by the
  press."

Do you really think a politician appealing to an imagined past is somehow unique or novel or goes unrecognized by the press? "Make X Great Again" is the oldest political slogan, ever. It implies your opponent is culpable for whatever ills people perceive, while simultaneously implying that he can make things better. Make what better? Things, just like they used to be! How? By restoring the past, d'uh!

And absent mental illness, few people's motivations are as specific or esoteric as you argue Thiel's motivations. It's important to realize this, because it explains why it's so easy (and usually so meaningless) to accuse people of petty contradictions. You'll always find contradictions between behavior and ideology if you assume the latter to be as specific as the former. Conversely, if you make the opposite assumption, or whitewash or fill-in the gaps of someone's ideology to make it more specific, you can rationalize their behavior however you want. That's what Trump's base does, and maybe what you're doing wrt to Thiel.

Unless they have some form of mental illness, people usually have very abstract ideologies and motivations made concrete and specific by context. However concrete you think an idea is in your head, it's not. It's a mental illusion. If you want to understand why Thiel is supporting Trump, the place to start is with the fact that Trump is now the President-elect. And that Thiel, like everybody, is fundamentally an opportunist. And that many successful people are especially good at seeking out and discovering opportunities, balancing agility with focus. One thing we can be sure of is that Thiel sees opportunity with Trump. Trying to pin-down precisely what that is, or even assuming his aims are yet concrete, makes the same error as you accuse journalists of making.

Also, the term "technology" in economics doesn't just mean inventions and science. It also means process, like democracy, bureaucracy, or management style. Or culture, like admitting women into the workplace. Technology, in the vocabulary of economics, is a word that describes an outcome--improved productivity leading to a net increase in social wealth--not necessarily anything specific or even physical. Maybe Thiel believes technological progress has plateaued in America, but getting from there to why he supports Trump is quite a leap, whatever his philosophical predilections.