I agree that Digital Ocean, Substack, and so on still operate as "chokepoints", and that I'd be more hardcore if I really went full-on setting up my own physical machine and my own totally open source web stack. Unfortunately, all of the software in that space is depressingly terrible - surely partly because of the mess that is the web - and it entirely lacks a good user experience, which is a very good argument in favor of these centralized services. For that reason, I've instead favored such centralized services, which is unfortunate but more practical for me, because I am a moron when it comes to running servers.
In my mind, the vision of fully decentralized self-hosting computing will simply never happen as long as this unfortunate technical situation remains - at some point, someone is going to have to really sit down and iron out all of the details in a way that doesn't absolutely suck shit. Like I mentioned in the article, Caddy and Gitea have done a fairly good job at the first few steps, but the tech and generally the whole process is still pretty idiotic, and I'm pretty sure it doesn't have to be.
2. his argument for moving away from MS GitHub is based on the understanding that license enforcement is lax in the modern era. the reasons he can expect to have greater license enforcement on a VPS than on MS GitHub may be real, but aren't immediately obvious to me. the most bulletproof defense seems to be one of obscurity: it takes a VPS provider more effort to decode his git repos than it does a managed git provider. any other defense i can come up with for why a VPS would enforce data agreements ought to apply similarly to GitHub (which is evidently not true).
i admit that a VPS achieves certain things better than self-hosting (as you say, it's easy to migrate, or deploy to multiple machines and have failover/load-balancing, etc). if the author is making a tradeoff between that and his license ideals, then his current solution might very well be right for him. on the other hand, if he prioritizes his license ideals as much as his post makes it seem, then he's already done half the work to go full self-hosting and may as well take the next step (as he says, "one day is worth it for a project that's going to have 10,000 hours of investment").
ownership is thorny (as the author is discovering). how does this change if you co-locate your box on the property of an internet exchange not owned by you? how does it change if you maintain physical possession of the host but there's some lien on it (i've never heard of somebody mortgaging a server, but there's no reason you couldn't)? i'm not sure. i think the concepts which "self-host" acts to label necessarily lie on a scale. if i were to attempt a strict boundary to which everything on one side is "self-hosting" and the other is not, there'd sure to be some contradictions. but i think at least notional ownership of the host is necessary for self-hosting and no VPS claims that.