Actually things have improved considerably this year. You may still not have the latest OS version, but the security patches are arriving every 1-2 months.
Oreo is supposed to improve things even further, but for know its just a theory.
"Aetna now reportedly has ambitions to offer it to a wider field — adding large swaths of new health data to pull from and giving the health insurance company insight into the activities of its customers."
This question is brought up every time this happens. Ubuntu uses stable (old) versions and does not upgrade to latest (unstable) releases very often. However, they do back port and apply security patches to these old versions.
Point in case: 16.04 TLS is still on 2.7.4 but it is fully patched and secure.
> but I never quite got into the tinkering culture
off topic (bikeshedding?) comment: you don't need to tinker with linux: install ubuntu, use it, profit. At work we went from "windows 8 + osx" to "ubuntu + windows 10". Nobody tinkers with anything and everything just works. Its just a bit faster and cheaper now.
I once was at a place were designers always had the last word (maybe because CEO was an architect), hence their new offices looked like a much cheaper version of Starbucks. With fewer couches and the few walls that made it were all made of glass.
The company is no longer around. These days just nearby their old offices brings back horrible memories.