I've not experienced something on this scale for many years, "Debian stable packages are so outdated" is mostly a meme. Debian 12 was 1y old when I did this and very often you can relatively easily find a backport or build one - but I think in this case it was either glibc or kernel, that's why "just run upstream" didn't work.
What’s the point of using a distribution if you need to find back ports or build your own? Distros are, after all, mostly collections of installable software.
The point is that it works 95% of the time, or probably more like 98%.
If this is a e.g. webserver and I only need my fastcgi backend built by myself, I can still have reverse proxy, database, and every other package be done by the distro.
No one said you need backports. More like: If it fits 90% and one package doesn't work, you get it from somewhere else - that doesn't invalidate the concept of a distro for me. YMMV
Honest question: wouldn't that make you more nervous you now arrived at an unknown/unsupported configuration?
Boring stability is the goal, but if Debian does not fit as is, then why not find a total package that is somewhat more cutting edge but does fit together? Especially given the fact that Debian does customization to upstream, so esoteric times esoteric.
It doesn't make me nervous because Debian has only let me down a couple of times over nearly 20 years and for example Ubuntu und RHEL and SLES have let me down dozens of times each.
Also I don't usually run "supported". I just run a system that fits my needs.
I maintain a couple of Debian servers and this is how I do it too.
Reverse proxy, DB, etc from Debian. The application server is built and deployed with nix. The Python version (and all the dependencies) that runs the application server is the tagged one in my nix flake which is the same used in the development environment.
I make sure that PostgreSQL is never upgraded past what is available in the latest Debian stable on any on the dev machines.
