I've found that the many of the relationships I'm most proud to have in my life are with those who had a reputation for being difficult and/or insufferable.

I think about it as a zero sum game: it seems impossible for someone to be stronger in some ways without being weaker in others.

Sometimes, with people who care to do so, they can work on those weaknesses and find ways to limit their impacts on themselves and others.

But everything comes at a cost.

Takeaway: if at least some of your friends aren't difficult in some ways, you're missing out on a lot.

Weird flex but ok. I think though that there is some merit in being able to communicate with a difficult or insufferable person but I find no merit can exist in choosing to take pride in regularly willingly doing so.

Well, presumably there are other aspects of those relationships to take pride in. You’re coming across as needlessly suspicious.

The value is that reputations are rarely indicative of what they appear from the surface; a lot of the time the reputation for being difficult ultimately derives from challenging polite bullshit, and in my experience _that_ correlates to deep competence often enough to be worth investigating.

Yeah, it took years for me to understand that the only people telling me things like "You always want to be right," or "Stop questioning everything," etc. as a child, were in fact themselves narcissists, abusers and control freaks who despise resistance.

I don't mean to make it sound so one-dimensional or axiomatic, but at least in my particular life, this turned out to be the case. I maintain an extremely close group of friends, the only people I find myself having problems with are typically those with some sort of personality disorder or malevolent intent. And boy, do those people have mean things to say about me. :)