When you say "out of date", you probably mean feature wise, not security and stability wise? For me that is an acceptable tradeoff for most of the packages. Most of the stuff doesn't evolve at such pace that I should have the latest and greatest (I am talking about core libs and similar). And the packages where I miss some new functionality, I can just upgrade them manually. Take Firefox for instance - if you don't like/trust Iceweasel, you can just install FF to /opt/ and trust Mozilla for upgrades. For me this is win-win situation. You have a stable and secure foundation and you put bleeding edge stuff on it when you need it.
Indeed, for myself I prefer stable releases (Debian, Ubuntu LTS, etc) and use apt pinning so that I can use newer versions of apps that I need to use. Very rarely will I have a problem; in fact the few times there is a problem it is normally solved by apt-get source ; dpkg-buildpackage.
It depends, normally in order of preference LTS, LTS backports, then latest release. So then if you want the newer version you can do apt-get install <package>/<release>. I typically use Apt::Default-Release "<release>" in a separate apt.conf.d file.
Just yesterday I had a problem which was some combination of Debian Jessie's incredibly outdated Python CFFI library (0.8.6) and its interaction with OpenSSL which took a script from taking milliseconds to launch to over 1.5 seconds, purely due to that import.
