You're entirely right about the importance of context. I grew up the opposite of conservative, yet I've learned very similar lessons. When you're on relatively equal footing with shared goals, most can become your friend. When there are power dynamics and the perception of a zero sum game, most can become your enemy. I've long been a person who seeks out those who are most opposed to my way of thinking, and I've never regretted being friendly with and understanding those people.

At the same time, getting into such neutral conditions is harder than ever for me, as the barriers get put up long before I show up. It's not actual conversations that hold me back, but getting there in the first place. Whenever I come across a conservative I can approach, I always make sure to talk with them.