This post is probably going to seem really random but I find your question thought-provoking for both personal and intellectual/academic reasons, so here goes:
When I was hangin’ with the Jews a lot (long story), I remember hearing that there was a rabbinic tradition that Paul had been “planted” among the Christians to corrupt the faith. When I became a Christian, I saw what they meant: Paul seems really different from everyone else who writes in the NT. I’m not saying I agree with that rabbinic tradition, just that I sense the same disconnect you do. I’ve always struggled with Paul (not least because of his page-long sentences—I mean really, punctuation is free, Paul!).
On the academic note, I wrote my dissertation on a church topic (though I did not study theology). Basically, I applied a sociological theory of organizational structure to the church. I didn’t do much with the early church, but what I did say there was that when Christ ascended to Heaven, the “charismatic” period of Christianity ended and a kind of institutionalization began. “Charismatic” in this sense doesn’t mean what Christians normally mean by it: It means that the ability to follow the “original founder” of a religion or organization or whatever has ended (or in this case, at least fundamentally changed) with the now-physical absence of that person. What happens in that person’s absence is pretty typical historically: The community tries to continue to live the life the founder preached, but if they’re going to endure as a community without the founder’s personal “charisma” there (in the flesh) to bind them, they need to create “structures” around the community that will hold them together. So they start meeting in fixed places (at first homes, then church buildings), start assigning “offices” to people to do the work of the community that previously people had just volunteered for (deacons were the first in the NT, and then that turned into priests), start coming up with rituals that define them and distinguish them from others (just look at all the stuff in the Catholic and Orthodox churches), and start making all kinds of rules about who can belong inside these structures and who doesn’t belong. In the absence of the original founder’s charismatic presence, these are the things that give order to the community. (And yes, there is a sense in which they are quite earthly… but I’ll stay off that soapbox.)
From that sociological perspective, Paul is an institutionalizer: He is the only Apostle who did not know Christ in the flesh, so he probably saw this whole Christian community thing very differently from those who did, and his tendency to set very clear rules definitely displays a “post-charismatic” tendency (again, in the sociological sense).
In the past few decades (well, ever since the Quakers, really), there’s been a strong tendency to undo the institutionalization of the church to recover a more “charismatic” (in both the sociological and Christian sense now) approach to faith. That being so, it’s no wonder to me so many people struggle with Paul today.
Not sure how clear/helpful/interesting that is, but I do tend to see the issue from both a theological and sociological perspective, and the latter helps me deal with the struggles I have with the former.