Again, we're talking about blogging, not business sites or SSR or CMS tooling. Very different needs with very different solutions.
I personally don't think it's that much work, and definitely not complicated, to keep my software up to date. And as a blog all I need to do is cache / throw behind a CDN and I'm golden. Nothing complex going on here. No headaches, no late nights, not even a wink of worry.
I think you two are talking past each other. Yes, people use WordPress for serious websites, and WooComerce stores, and all that stuff. But Tallain is not talking about those people. Tallain is talking about blogging.
Blogging is also often business critical. Entire businesses are built around blogs. I presonally know someone who sold their "wordpress blog" for $30m.
I personally don't think it's that much work, and definitely not complicated, to keep my software up to date. And as a blog all I need to do is cache / throw behind a CDN and I'm golden. Nothing complex going on here. No headaches, no late nights, not even a wink of worry.