Off-topic, really, as the Codex doesn't figure into this discussion in any way. I'll just say that it is by far the largest and the most active of the communities that I host, so it has some specifics that differ compared to all the other websites that I host. It also occasionally requires specific software and hardware upgrades, custom work, etc. that quickly translate into thousands of dollars of expenses and/or hundreds of man-hours of work due to the heavily modified and custom-coded environment. This is something that websites run on a shoestring budget with volunteer work only usually can't afford to do, so they either linger on without doing the necessary upgrades and improvements for years, or end up closing down once maintenance becomes more trouble than it's worth.
Transitioning a website from one generation of forum software to another along with the entire back-end dependent on it is one such major step that requires an insane amount of time and effort that mostly happens behind the scenes, so the end users can never really appreciate it as they will only see a fraction of it. Everything else needs to happen on the back-end, behind the scenes, and it's a daunting project even for an experienced team, let alone one or two people working on it, as is usually the case with small independent websites. I've been there and done it myself several times, so I've got plenty of first-hand experience.
Naturally, there will always be naysayers and second-guessers with their own view of how it's all just fun and games with no effort required and ideas how they would do it all better, cheaper, more effectively and so on. But that's just part and parcel of being on the internet, where talk is very cheap. In the end you either put some trust into the person who is ultimately responsible for the whole website, or you don't. I've been at this for 23 years now, so I'd like to think that that counts for something.