After about nine years of writing, I've concluded something similar: my existing reactive approach (https://www.gwern.net/Archiving-URLs) is not going to scale either with expanding content or over time. Fixing individual links is OK if you have only a few or aren't going to be around too long, but as you approach tens of thousands of links over decades, the dead links build up.
So the solution I am going to implement soon is taking a tool like ArchiveBox or SinglePage and hosting my own copies of (most) external links, so they will be cached shortly after linking and can't break. The bandwidth and space will be somewhat expensive, but it'll save me and my readers a ton in the long run.