Seven years into a project is an insane time to find out that numerous art assets are missing or corrupt, or that an earlier coder was using undocumented naming schemes, or any of the other bits of ridiculous development malpractice that have leaked out on Discord or Picarto streams.
Most of this has been well known. Some people here really seem to forget that DC started this whole game to teach himself coding and that all of the coding that was done in the first year(s), was done by someone who happened to be part of DC's early chats. Comparing that to any kind of professional work ist really besides the point.
Next to that people tend to forget, that DC struggled with the thought of a tech update before this one happened and that Patreons did vote against it, the first time he polled it. Which, by the way, was celebrated by most of the people who already screamed "he's milking" back then...
Having a good project manager makes everyone's lives easier because it removes uncertainty and redundancy and keeps everyone to a schedule. My own job would be impossible if we didn't have an admin staff keeping everyone's docket up-to-date; I'd spend half my day organizing my calendar otherwise.
I think it's important to differentiate between working in larger teams/companies and working in small teams. You don't need a manager in a semi well orgranized team of 3 people who are on good terms. You need someone who takes decisions and who holds people accountable and that's really it. That's clearly DC's job.
If DC didn't manage to make Dogeek work properly (I've seen them "argue" a few times in chat/stream), you think some random hired manager would have managed that? Nah. Again, you can't compare indie development to some kind of professional work environment - it'll never be the same.
What DC should have done, is getting a consultant/dev/coder who knows how to run large(ish) coding projects and who knows how to work with python/renpy, so there'd be workable roadmap for the tech update and he should have hired someone to prepare a lof of the stuff that's causing problems now, while they were still working on the main story. But that's something very different from having a manager in general.
The tech update isn't struggling because someone isn't keeping his deadlines or doesn't do what he's supposed to do, but because they fundementally, massively missjudged the work that had to be done before they started and had to figure all of that out while they had were already working.
Just to add:
I don't think DC personally cares thaaaaat much about all of that anyway. And we shouldn't either, to be honest. As long as he's creating assets for the game, the content will ultimately be released. If the tech update had been on time, there's a good chance we had never gotten some of these pre-tech scenes, for example.
After all, the only thing that's hurt by this delay is his financial bottom line and that's really only his personal problem.