Edit: And later on...
The individual releases of a given distribution are much more independent of each other, so it's harder to turn your RedHat 7.3 system into a RedHat 8 system. [...] With a Linux system, however, you tend to find yourself trying to keep a handful of obvious things upgraded, while others get further and further behind, until eventually you just reinstall with the latest version to bring it up to date.
That may be true for RedHat (which I've never used), but Debian has always had good old apt-get update && apt-get dist-upgrade to bring everything up to date.
Edit 2: Whoa, randomly changing site theme.