I think you're a hell of a lot closer than most Christians, but my read through was different when it came to Rome

Like when they asked if they should pay the tax collector. He asked who's head was on the coin, and said "give unto Cesar what is Caesar's". My teacher said that means pay your taxes... That's a pretty strained reason

What he was saying is "let's just share among each other, then coin means nothing to us". He was advocating dropping out of the Roman economy

He also preached that if you have excess, you share it generously - so no huge stockpiles of grain to be seized.

And it was like this across the board - we don't need temples, it's enough to share a meal. We don't need the holy of holies or complex bathing rituals - here's a new ritual that only requires a bit of water

We don't need leaders, if we all focus on serving each other everything will fall into place.

If Romans demand work from you, use their laws and customs against them. Make it frustrating to deal with you while giving them no justification to draw a sword

It all fits together nicely. It's not about religion - everything he said on that topic boils down to "you've mistaken our laws for the meaning behind them and they've become a reason to do evil. At the core, it's just be good to each other, everything flows from there"

Jesus was a revolutionary. He sought to free his people not as a heroic warlord, but by making them unprofitable and frustrating. He was removing the weaknesses of his people. If you have no leaders, there's no one to hold hostage. If you hold the spirit of the law above it's wording, the religious leaders couldn't demand obedience through religion. If you give away your money freely and have no big stores of food or wealth, there's nothing for them to take. There's no handle to control them, and there's no profit in raiding them

And that's why he died - it seems very clear to me that Judas didn't betray him - he followed Jesus's plan. Jesus warned them all it was about to happen, and told them not to resist. Judas didn't want the silver, he felt enough guilt/grief to take his own life.

Jesus himself was the last weakness, so he had to die. Or at least stage his death - he was very popular among the legions very soon after his death. Maybe he had inside help from his executioners, he was up on the cross for a very short time (granted, he was probably on the verge of death already)

Unfortunately, it still had one weakness... The Romans straight up brutally massacred his peaceful followers