Hmm, interesting that you both agree on Discourse being easier to use/admin than Wordpress. I don’t think I do, and there are a couple of aspects to that. It starts at the beginning, the install level, which is pretty inarguably in the favor of Wordpress for ease of use for a few reasons: its hosting environment (LAMP) is far more widely supported, many web hosts now have turnkey “Install Wordpress for me” tools, and even a manual install is generally easier with the availability of file browsing via control panels and PHPMyAdmin. Compare that to the command line requirements of Discourse.
Not to mention updates. I’ve had a few Wordpress sites for nearly a decade now and have very seldom run into issues with automatic updates. These days the web hosts often just keep things updated for you. After running a Discourse site for several years, I ran into issues updating through the control panel often enough that someone not savvy with the command line would be utterly lost trying to be a Discourse admin. I had to learn a lot about working with Linux, and to some degree I’m glad I did, but for most people it’s going to be too much.
Then there is technical support. Again there are many, many Wordpress-dedicated web hosts who will help you with WP issues via their native support. And if that’s not available, you can hire someone and there are a lot more options for consultants and they work cheaper than Discourse experts. Not surprisingly, and I’m not criticizing Discourse consultants, just stating a fact. That said I will applaud Discourse’s support community here in Meta for being a better and more discoverable one-stop for answering most Discourse questions, vs. the much poorer Wordpress “forum”/discussion experience for finding answers outside the norm. Reddit for WP of course has a comparable utility, but at least CDCK maintains an excellent single source for deep discussion and troubleshooting here.
Now outside of install and updates, I’d say they’re more comparable in intuitiveness and ease of use/admin. I certainly can’t see a super clear advantage to Discourse, except perhaps in some of the complexity of options WP has in Gutenberg these days. Discourse’s setting search and other things do make it easier to do certain things. But at this point I think the comparison fully breaks down, they’re trying to do very different things and the customers coming to them are doing so for different reasons in the vast majority of cases. I honestly don’t know how useful it is to continue using WP as a comparison.
The real question is what are prospective community admins/managers/founders choosing instead when they setup a community, and while it’s true that Reddit/FB/etc are common, that’s also not actually what is necessarily being raised by OP (and in the similar thread I linked to earlier). Anyone looking for a free community is going to choose a free option, which is basically Reddit, Facebook, or Discord. Anyone looking for an Enterprise solution is going to consider more customizable platforms, Discourse among them. But there is a decent market of people in-between that - and I have been part of this market off and on for a long time - of people who want a better or more customizable or just private community, or who want to own their data, or both, who are willing to pay to setup and maintain a good system, but whose budget is still limited, and often tech skills are a bit more limited too (vs. an enterprise customer, for example). This is the “Medium” in the title here, I think. And I do think they could be better served by Discourse in various respects; in ease of install and maintenance; in price; in theming improvements; etc. Much of this is discussed in other threads already linked in this topic.