I think you’re right about the rose-colored nostalgia: it’s easy to forget how far behind people got on updates. I remember so many support emails where someone had hit a bug which had been patched a year earlier but never thought to install it. A couple of times where people reinvented something which had been added to PHP in the meantime because they didn’t know it was there.
That’s why they keep it private by default, but the answer is often yes. There have been multiple times where a package like Python 3.10 required a newer version (1.1.1) than the OS release included (I suspect that’s also why the AWS Lambda runtime is stuck on 3.9 since it’s based on Amazon Linux 2 and that uses 1 .0).
This has settled down a bit but the big HTTPS-everywhere push last decade flushed out a ton of things which had been quietly aging in place, unnoticed until someone started depending on SNI, newer crypto suites, actually disabling deprecated versions of SSL/TLS, etc.
Maybe it’s quieted down recently after the HTTPS effort, but I feel like I need to download a whole Unix environment, down to the readline, every now and then when I just wanted to install a trivial thing.