I've traveled the world this last year, and have certainly experienced all sorts of stupidity, ridiculous bureaucracy and corruption in this regard. Like OP I discovered that I enjoy going through these Kafkaesque mazes, and found it pretty fun. Literally never knowing if I'm passing a border post or having to turn back (spoiler: I never turned back).
That said, I didn't go to any of the east Asian countries, because it would have been "too much" (as is clear from this post).
In Latin America and Africa, all the "covid policy" was just a clear corruption opportunity being taken advantage of. More things you could "do wrong" is a big boon for every corrupt official. In Africa, border personnel were happy to take a bribe as your "PCR test" (and the one time I actually did a PCR test, they did not accept it, they only wanted the bribe). Police were happy to enforce the mask rules (on white tourists only, in the middle of the night). Businesses were happy to convert to a "PCR testing clinic" by painting the walls white, sticking something in your nose, and giving you a piece of paper for money (even if you wanted a real PCR test, you couldn't know it's real). You see the picture.
Thing is, I've learned that the overt corruption in these "developing" countries is just less sophisticated version of what's going on in the rest of the world. So, the next time you encounter bullshit like this, just try to ask yourself why are they doing this? Who gains from this? Etc. It's a fun game, and sometimes you come to interesting realizations.