I'm only vaguely familiar with Tailscale, but I am very interested after reading this and will seriously look into it as soon as I have proper time. The author makes a lot of excellent points, and very directly explains a lot of the problems I have with modern computing.

As an industry, we’ve spent all our time making the hard things possible, and none of our time making the easy things easy.

This has been the trend for literally the entire 21st century so far. I'm also one of those "mature" computer users. I started coding before JavaScript was even a thing. And I've been repeatedly shocked and frustrated at how things that took me literally one line of code in the 90s somehow require entire custom classes built atop massive frameworks today. Dude, all I want is to add a row to a listbox. It's not rocket science. I don't need it to be performant with millions of rows. It's only going to have, like, ten. This does not require data providers and callbacks and backends. (I'm sure there are modern frameworks that make this easier, but this is a real-world example from the Objective-C/Cocoa era of Mac OS X. Not coincidentally, I stopped caring about writing GUIs around that time.)