[AdmiralAsshat]

Previous product I worked on required a supported RHEL/CentOS environment on which to install our product. Even with the six years or so of support, our customers would piss and moan every time we'd tell them that RHEL/Centos5 was hitting EOL and they'd need to upgrade their servers to Centos 6 or 7 to stay supported. Most of them wouldn't even entertain the idea of "upgrading": for them, business as usual was holding on to the existing OS as long as possible, then buying an entirely new server with the latest-greatest CentOS release freshly installed on it, and doing a data migration.

I can't even imagine the amount of headache we would have gotten if they needed to upgrade every two years.

[mixmastamyk]

When you update often it turns out to be less work, because more gets automated and changes are smaller. This is the CI/CD proposition anyway.

[AdmiralAsshat]

Except when the update brings some kind of massive change. RHEL 6->7, for example, was when systemd became the norm, and so right around the time our customers started upgrading, I suddenly had the hot potato dropped into my lap of needing to convert 20 years' worth of our software's init.d scripts into systemd services.

[mixmastamyk]

Debian, Ubuntu handled those side by side for a while, surprised RH didn’t.