Yeah, absolutely. I think this is the only way (or at least the best, most reliable way) to influence people. Trying to understand the perspective of people you disagree with is the first step in encouraging them to understand yours. That's why I'm often mistaken for a centrist when what I actually am is somebody who tries to see both sides. Even if I usually land pretty squarely on one. Politics has sadly become a game of no compromise and no empathy.
I'm not sure what conversations I've engaged in with conservatives that would be controversial. Not even sure how many conservatives are in my audience to be honest. Though that word tends to get thrown around pretty loosely nowadays. But if people would run me out of town because I had a conversation, I would have serious doubts about whether they're my people.
It sounds like you're doing great work. I agree that systems are vitally important. I wish you all the best. Keep bending the arc of the moral universe. 👍