The ribbon really isn't the same thing as a flat look. The two are totally independent of one another. Take a look at this screenshot, for example: Windows 7 with visual styles turned off—no doubt familiar to anyone who's managed a recent Windows Server or used RDP. It's still full of the newfangled conveniences you loathe, despite being cast in traditional 90s bezels.
This is the point where the holier-than-thou crowd says you should know all the hotkey combinations for everything if you want to be efficient. Those never changed, creating a nightmare for anyone who wants to learn them in the post-ribbon Word.
Almost all of the biggest offenders were iOS apps, so if you never had an iPhone you were spared the vast majority of incidents where skeuomorphism caused problems. Ideally, you're right, skeuomorphism should be helpful, but many designers used it to create the illusion of quality by borrowing images and textures from physical objects that they perceived as being valuable. Here is a thorough breakdown of the nausea of the era.
It's a little sharper than that—the current generation of interface designs was a direct reaction to the previous decade's tradition of absurd skeuomorphism. The moment Steve Jobs died, Apple did an about-face and started following Microsoft's Win8/Modern/Metro UI lead. It may look like a step backward to those who from the Windows 2000 and Gnome 2 era, since there's a loss of visual cues, but the flatness of current interfaces is way better than what the classics became in the post-Windows XP era: bloated, overdesigned, pseudo-real-objects cluttered with mismatched shadows and conflicting perspective angles. You couldn't tell what was a button there, either! At least now there's a consistency and a return to the actual use of design guidelines.
That said, there are still a lot of cases where literacy in idioms dominates: for example, the largely inexplicable convention of swiping sideways on a list to reveal 'delete' or 'edit' buttons in mobile apps. That's probably where you and the UX designers run into the most difficulty. But two decades ago, every "how-to-use-a-computer" class targeted at seniors started with how to operate a mouse—so, as I think you've already recognized, it's important to try to take these things with a grain of salt, and recognize that no one is completely objective when it comes to understanding the culture of computer operation.
Of course it's unrealistic armchair-libertarian drivel: the magnetosphere is a harsh mistress, after all.
What's interesting about this development is that it isn't a nearly-entirely American endeavour, which is often the case with such ambitions; Asgardia seems to be Russian and the AIRC supporting it is Viennese. I suspect we'll see a lot more anti-authoritarian behaviour from Europeans in the coming years as a) the EU weakens, b) the Internet transmits political memes that were previously comparatively contained by media limitations like talk radio and poor English literacy, and c) people already exposed to (b) come of age.
The much more feasible version of "let's get off the Earth so we can get away from our countries' laws" is called seasteading, and generally involves a platform in international waters. There's one clear non-Libertarian, non-American example of seasteading (Sealand, UK) which is fairly old and unusually successful by micronation standards. These days, however, the idea is generally associated with these guys, who have been funded by Peter Thiel. They, unquestionably, are primarily concerned with ways to dodge regulation. Without a realistic means of building such a gigantic physical presence, though, they certainly aren't going to be doing much of that; at best they'd end up creating their own passports that no one would accept.
We can defeat gravity. The problem is the paperwork involved.