Having learnt my lesson about staying up to date so as to not get stuck with a hard-to-upgrade install, I set about upgrading my Debian “server” to Jessie. How about that for ease?

Add a few lines to a config file (etc/apt/sources.list, to tell it where the updates are), apt-get update, apt-get upgrade (a cautious intermediate upgrade), apt-get dist-upgrade, answer a few questions, and off it goes, with 1 reboot (for a kernel change), and all services working with short interruptions only, and remotely over ssh, and only a couple of hundred MB download to have the latest release- running on antique hardware.

That’s how an upgrade should work.