Medium is definitely a diverse crowd... and there's various qualities of writing. Some of the best thinkers aren't the best writers, and some of the best writers aren't the best thinkers. There's a sensible middle ground though and I think the most interesting voices fit into that place on the platform. I'd put both Steve and Katie in that sweet spot - whereas others (like Jessica Valenti) write well but can't think their way of a paper bag. One of the biggest frustrations I have is that those who have interesting thoughts - sometimes miss the fundamentals of writing. Titles. Pictures. Breezy prose. Some people are a hard read - so it doesn't matter from a Medium perspective what they go on to write.
I don't think the vast majority of people could make a living here - and those who do are at the whims of the algorithm changing and the rug being pulled out from underneath them. Shannon Ashley is a good example of this in action, making a fortune until she wasn't. I'm sure she's still doing okay, but she's not making the vast sums she once was.
I think Medium are working on getting people to find their audience - the problem is there are multiple audiences on here - and some people chase those audiences creating a positive feedback loop. That's why you'll see a lot of 'how I made $200 with one post' type articles. A writer accidentally writes something successful, then realises that writing about their success also has an audience. The gravitational pull of those sorts of articles creates little room for genuinely interesting stuff to emerge - I think Medium are working on it though. They have to be, gives us all a bit of hope for the future.
Always happy to chat - that's one of the things Medium is for. :o)