These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
YMMV: The Dispossessed
Critical Research Failure: Shevek floors an Urrasti in debate by pointing out that military hierarchy is unnecessary, since, after all, guerrillas manage without such things. Apparently, Ursula K. Le Guin had never troubled herself to learn anything about guerilla warfare, as even a cursory study of the topic would have taught her that guerilla armies do indeed have rank structures, organized units, and hierarchies of command (they are basically just light infantry who are trained in raiding tactics). This was an especially egregious error, given that America was actually involved ina guerrilla war at the time that she wrote this book — with guerrillas who had a very highly developed military hierarchy.
To be fair, there are historical examples of guerrillas who didn't use hierarchy, like the POUM militias George Orwell fought with during the Spanish Civil War (read Orwell's Homage to Catalonia for a detailed description). Of course, they lost the war.
Debate and Switch: Most of the book can be read as a dramatized debate over the question of whether anarchism, represented by the Odonian philosophy practised on Anarres, or liberal democratic capitalism, represented by the nation of A-Io, is better. Although it is clear that the author's sympathies lie mostly with Odonianism, the question is dealt with subtly, with the increasing majority-backed repressiveness of Anarres being shown, as is the fact that the profit motive as practised on A-Io provides a far better life to most Iotians than Shevek had been led to believe. Then, practically out of the blue, A-Io massacres peaceful protestors by the thousand. Well, duh, Anarresti anarchism is better than that. So, for that matter, is the United States of America in the 1970's, for which A-Io was obviously meant to be a loose analogue. Hell, by the 1970's even the real-world analogue of Thu, the USSR, was not mowing down protestors in such numbers that the closely-packed dead bodies were left jammed in a standing position. The whole philosophical debate is tossed aside and replaced by Baddies Are Bad.
In an interesting case, the A-Io's actions are understandable, though not justified - they remember what the last strike led to, and they are all out of moons to bribe dissidents with.
It's probably worth noting that, while massacres of striking workers weren't common in 1970s America, they were common in America at the turn of the century, so this could also simply be a case of Anachronism Stew.