I find the whole thing funny. There's not so much secret sauce going on here as much as you might think. I've been reading Daring Fireball for a long time but I think anytime you make this suggestion the automatic response is to think there is some shady cabal behind the scenes and that's just conspiracy theory stuff. Anytime someone makes a meta post questioning how HN ranks articles it almost always gets flagged because it's not really on topic.
I don't have nearly as sophisticated setup as [Gwern](https://gwern.net/archiving), but they provide an overview of how you might go about it. Right now I manually use the extension on as as needed basis, but I would like to get it to the point where I can point a script at a list of urls and both run SingleFile and also upload to the Wayback Machine
It really depends on your needs. I use Pinboard on many different browsers and devices and I'm not really interested in running my own service. I'll happily pay for the full text archiving but I acknowledge it is not perfect. I have come to the conclusion if you want to retain full text copies of your bookmarks, you need to download the pages yourself. I have been using SingleFile extension but there is also a CLI available.
The bigger issue is on Apple and iOS, the "regular user" doesn't often interact with individual files outside of the app. Even at my work (US airline), there have been recent restrictions added to the workstations so you can't just plug in a USB thumb drive and transfer some files (honestly a no-brainer). But for many people, much of their experience learning about using computers comes from work. If you don't regularly do it at work, how would they learn how to do it outside of work?
It's interesting to read the criticisms of NaNoWriMo because they don't really change. I have completed it for 15 years in a row, then on year 16 I sort of hit a wall and this year I am deliberately not doing it. But my friend and I have been doing it since high school. The point is usually not about doing it to become published but rather to have fun. I'm not sure if I would have been able to do it without going to some of the in-person write-ins. I even know someone who met their husband at a in-person write-in.
I have been using [Jumpcut](https://github.com/snark/jumpcut) for this purpose. I have it bound to ctrl cmd v, so it doesn't conflict with the normal cmd v