Personally, I just go for "plateaus of understanding". As a filthy socialist in a deep red area, I never had a chance at convincing people all in one go. So I give them just enough that they'll come back around for another bite at convincing me why I'm wrong. Where I'm from, that mostly looks like waiting on the news cycle to say something bad about a democrat and then letting them bring it up purely to dunk on me, rather than to actually engage with the conversation. So I take the opportunity to redirect the dunk. "Oh, that IS bad. Wow, they really fucked up. Isn't this like how So and So did something similar?" Now they are explaining to me the nuances of difference between the situations. That's what they'll remember later - the arguments THEY made. And when they start comparing that to other things, reason wears them down like it does anyone else.

In effect, you end up getting them to agree with some otherwise unthinkable positions, just one plateau at a time. There's only so much erosion that can take place before they fall back to their own lines of thought termination (like "all I care about is immigration", or whatever). So you end up with a kind of "anchor" that we can both agree on (ex: corporations are fucking us), which still has the hard edge of politics. At that point, all it takes is for the politics to do enough that the hard edges start to erode. But, there's no accounting for that. Just gotta assume the people who are doing wrong will keep proving it (as they historically have been unable to avoid, no matter how hard they try or how long they are successful at it prior).

As you say: life is complicated. I know people will roll their eyes at this answer as much as any other response I could give you. And I know that a political-focused answer isn't directly analogous to many other situations. But, my answer is as simple as I can think to make it. Just meet people where they're meeting you and don't worry about forcing a point.