> Aside from the occasional annoyances of self hosting, that cynically I have suspected is just a way to drive users towards their hosted version

I'm a long-time Discourse employee and this is certainly not intentional, I'm obviously biased — but we help self-hosters out all the time for completely free on https://meta.discourse.org. We can't support every variety of configuration, but we consider every Discourse site progress, whether we host it or not.