I like my system to stay working and maintainable. I still have one system that was installed with Debian 2.1, and upgraded ever since and is still doing fine. You don’t generally get there by taking shortcuts that seem convinient now, even though long term they are a bad idea.
Sure. I have that religion too.
The other way that you don’t get to having a system that’s been continuously upgraded from Debian 2.1 is if you got fired somewhere around Debian 3 because you couldn’t deploy things fast enough for your boss, who didn’t give a shit about whether things were in Debian packages or not.