Writing this as someone who doesn't fall for Tolkien's romanticism of the past but nevertheless is a pedant.
I was reading about how Germanic societies worked before Charlemagne, before feudalism. And essentially what I ended up realizing is that this is the Rohan of Tolkien's world. Instead of a clear division between "warrior" and "farmer", the farmers were the warriors simultaneously. Free-born or freedmen. You are a free man, so you must know how to fight, to defend yourself, your farm, your family, your "people". Of course, I'm sure Tolkien wasn't a fan of the slavery practice, but the "heroic" free men are the ideal specifically.
In this model, the ruler is not your manager/boss, he is "first among equals".
Many haters of Tolkien seem to have the misconception that the Hobbits are his "ideal". But on the contrary, the Hobbits are the men who had forgotten their "heroism", who had become domesticated, dependant on violent men with swords to defend them. They are not what was "lost", that would be Rohan, they are the later stage transition to the "loss" of "heroic freedom", where the divide between farmer and warrior is now the rule (the warrior part of the equation being Gondor, themselves part of this "loss" of "heroic freedom").
So, to be pedantic, he wasn't "pro-feudalism", he was anti-Charlemagne (in the political sense at least), he would align himself with the freeman Stellinga revolt of 841-843, which I imagine to use an analogy, was something like trying to disarm Texans.
The irony of course is that Christianity/the Church played a major role in this domestication of the once "honorable" Germanic farmer-warriors. Tolkien was a devour Catholic.