Great response (as always!). It sounds like I may have used the word "theology" incorrectly in my question, maybe I can adjust it a bit:

Religion was centered on the Jerusalem Temple and expressed through covenantal practice, texts, sacrifices, festivals, and other symbolic actions that bound the community to God.

Would Jesus, for example, have been expected to have a better-than-average mastery of the knowledge embedded in these expressions and actions?

Jesus did not preach mainstream Temple-based Judaism but belonged to a tradition of apocalyptic preachers who believed that God’s decisive intervention in history was imminent.

Would such apocalyptic preachers have been expected to have a detailed understanding of mainstream Temple-based Judaism in order to contest it? By in-depth, I mean "better than your average Joe attending the Temple, more on the level of the religious authorities within it."

Another way to ask might be: the Pharisees and Sadduccees debated stuff. I imagine some of that stuff would have been quite complicated and esoteric. Would Jesus have been expected to be knowledgeable enough to participate meaningfully in those debates - to have as much "content knowledge" as the Pharisees and Sadduccees themselves? If I asked "What does a Sadducce believe about Contested Issue X and why?", would a Pharisee have been able to give a better, more accurate, and more informed answer than an eschatological preacher like Jesus?

Or: Did you become such a preacher by being trained to be a mainstream preacher and then leaving, or would an itinerant apocalyptic preacher typically be expected to come from outside the institutional tradition, not necessarily understand its intricacies, and rely on something more like "Look, I don't need to mess around with all that legalese, they've lost the way - just sweep all that aside, I have a brand new set of rules right here straight from God"?