I disagree about "DNs being the mainstream" and "a lot" of companies are working/hiring remotely. The number of companies and friends you know isn't big enough as a sample size. The ratio of companies hiring all in-house V.S. remote companies or companies that hire some remote people is still pretty skewed. Maybe someone can research into it, give us some numbers and prove me wrong.
My biggest pain point in the DN scene is that not enough companies are hiring people remotely, whether as an employee or contractor/consultant. Companies still have the old mindset that they need people to be in the office. I realized that (long ago) that I don't have as many inquiries when I accept only remote work compared to when I live somewhere for more than 1 year. If you look at any popular job boards, 90+% of them are tagged with a location and not "anywhere"; or you can compare the number of jobs being posted on remoteok and any normal tech job board (e.g. Dice).
I've been to many DN events/meetups and usually more than half of the attendees are not DNs who are travelling full-time. Most of the DN events are for nomad-wannabes to learn more about being a nomad. It's not a bad thing, but we need to prepare them (and others) for what happens after they decide to become a nomad. What if they have trouble convincing their boss, or trouble getting clients once they've gone remote?
I would love to see events/products/services being built/organized to talk about the advantages of hiring remote workers.
If there are so many remote workers and there are not enough companies hiring, eventually, some might be pressured to take a full-time in-house job or switch their career. And that's not what I want to do.
p.s. I know that remote company CEOs are interviewed in the DN documentary, but we're still waiting for that so.