> The hurdles are often organizational rather than technical.
Yeah. And in my opinion "organizational" reasons can (and should) include "we are just not at the scale where achieving that makes sense".
If you have single digit numbers of machines, the whole solid observability/ automated node replacement/self-healing setup overhead is unlikely to pay off. Especially if the SLAs don't require 2am weekend hair-on-fire platform recovery. For a _lot_ things, you can almost completely avoid on-call incidents with straightforward redundant (over provisioned) HA architectures, no single points of failure, and sensible office hours only deployment rules (and never _ever_ deploy to Prod on a Friday afternoon).
Scrappy startups, and web/mobile platforms for anything where a few hours of downtime is not going to be an existential threat to the money flow or a big story in the tech press - probably have more important things to be doing than setting up log aggregation and request tracing. Work towards that, sure, but probably prioritise the dev productivity parts first. Get your CI/CD pipeline rock solid. Get some decent monitoring of the redundant components of your HA setup (as well as the Prod load balancer monitoring) so you know when you're degraded but not down (giving you some breathing space to troubleshoot).
And aspire to fully resilient systems and have a plan for what they might look like in the future to avoid painting yourself into a corner that makes it harder then necessary to get there one day.
But if you've got a guy spending 6 months setting up chaos monkey and chaos doctor for your WordPress site that's only getting a few thousand visits a day, you're definitely going it wrong. Five nines are expensive. If your users are gonna be "happy enough" with three nines or even two nines, you've probably got way better things to do with that budget.