Star Wars: The Acolyte official trailer

[KorvinStarmast]

And I am starting to realize my whole problem with Star Wars is that the Jedi seem to be about collectivism, about letting go of your individuality and your emotions and listening to the universe as a whole, whereas as the Sith seem to be about individuality; personal strength and charisma and pursuing your own passions in your own way. But, on the other hand, the Sith support an oppressive totalitarian, whereas the Jedi support "peace and freedom" and support an ineffectual republic and a violent rebellion.

Violent rebellion is what often is resorted to that gets rid of tyranny. Suggest you read up on a little actual history of the actual world, your own homeland included. (Of course it holds the risk of "meet the new boss, same as the old boss" which revolutions aplenty have set up IRL).

It really leaves me confused as to which side to support. What we are shown doesn't really match up with what we are told.

Lucas was telling an adventure story, and I will suggest that you are overthinking this. The Sith aren't just about individualism, the Sith are about Power and Deceit, which are intended to lead to Domination of others. Those are their core values.

And then it gets even weirder when we get into slavery.

Slavery in a variety of forms is a human institution/practice that goes back to the Sumerians (at least). I think you'll find that in Star Wars, the Empire and the Republic were both Very Loosely based on the Roman Republic and the Roman Empire (pretty sure Lucas himself mentioned this decades ago) both of which had slavery. Also, as A Narrative Tool, being or beginning as a slave offers the Underdog Overcomes plot line a lot of room to work with.

Anyone else have any insight into what I am feeling?

My insight: you are overthinking this. Lucas, as a story teller, wasn't particularly good at nuance.

I don't think it's a fair read to say that the Jedi supported an ineffectual Republic, it worked very well for a very long time.

Republics tend to be a bit messy and inefficient, as does any representative form of government. It's a feature, not a bug. Autocratic forms are often "more efficient" but there is a cost to that. I'll stop there, must not drift too far into RL stuff. I am currently reading a scholarly book on the Eastern Roman Empire (I have gotten from about Diocletian (late 200's to Anastasios (early 500's) so far and while it's fascinating, I need to avoid mixing my media and my messages.

The element of Revenge of the Sith that is profoundly weird by most modern blockbuster standards is that the hero getting ultimate power to obtain everything he wants, free of limitation from others, is a bad thing. Having taken great power, the protagonist creates not justice but oppression. His willingness to do anything to save his loved ones is not strength and truimph but profound weakness and failure. Normally special magic chosen one movies, particularly in the age of Marvel, tell us pretty much exactly the opposite of this, if only the special people (meaning the audience surrogates) had ultimate power they could fix things, that anything done to save friends and family is not only justified but heroic because friends and family are ultimately all that matters. Often said in exactly those words.

I like your analysis of that.

One suggestion I have seen, vis a vis Anakin, is that the Dark Side won the Duel of the Fates with the death of Qui Gonn. Sure, Maul [kinda-sorta] died, and Obi-Wan "won", but Obi-Wan wasn't equipped to deal with Anakin, to train him well, whereas Qui Gonn was. Had Qui-Gonn survived, he could have guided Anakin through his tribulations. But he did not, so Anakin was left with "brother" Obi-Wan instead of "Father" Qui-Gonn.

Yep.

The Trade Federation

They illustrate the limitations of the Republic's reach and power.

I think it's depiction of the Jedi Order shows a greater number of unintentional points of failure.

Yes. Weaknesses hidden within.

Lucas is on record as saying he depicted the Jedi in a hope of fostering increased spirituality in his audience, which explains the Jedi Order's very obvious religious structure.

Indeed. In "A New Hope" (Original Star Wars Movie, Episode 4 ...) Tarkin early on makes a comment to Vader about his religion (with Vader being a Jedi).
At the time the movie came out, my take on the Jedi was a mix of "monks like Kwai Chang Caine with Magic also" combined with "psionics from D&D" (original game). At that time, Monks were not able to have psionic power (Eldritch Wizardry, Supp III to OD&D). IIRC, in AD&D 1e that restriction was lifted.

Later in life, I got a feeling that they were a bit more like 'Jesuits with Magic and Light Sabers' but that's not a great take.