> Unfortunately, like with all other bookmark-like services I have tried over the years, I did not use it regularly and it faded out of my habits rather quickly.
I think the key is not trying to use it to replace bookmarks. That takes deliberate work and commitment.
I began using Hypothesis to write "replies" where the comment mechanism was non-existent/unreliable/cumbersome (e.g. on very old content or HN threads, or blogs where the author is likely to not tolerate dissenting opinions, or forums where I don't already have an account, etc.), or instances where I couldn't resist jotting down a response that I had no intention of actually posting publicly (because e.g. being heavy on snark). Eventually you gradually build up a personalized data source that is richer than just the bookmark tagging system (and also includes pages things that you would never think to bookmark deliberately but have later discover some need to revisit it despite that—ever fished something out of your past without having bookmarked it, but were able to relocate it years later because you could recall something about an HN thread that you participated in?). I continue using bookmarks and tags—which, like you, I treat it as as close to a zero-friction act as possible rather than meticulously filing it away in a hierarchy. Using Hypothesis, though, is a supplement to ordinary bookmark usage—an additional resource.
> I might move on to a self-hosted bookmark solution in the future that adds the the option to locally archive a webpage
I recommend using Zotero to capture snapshots but otherwise continuing to use browser-based bookmarks. My relationship with Zotero is similar to Hypothesis—having known about it for years, I only started using it recently (ca. 2020). But it's great. I should've been using it all along.