Mechanic,
Having the documentation be outdated and not working with the current version is a problem for software all around the world. Even more so for an open source community. I completely agree with you that beginner samples need to be maintained so that they stay relevant to new versions of the software. Unfortunately, that is a very difficult thing to do. It would be nice to have a seperate version specific documentation section on the website and a team of people who would move the documentation forward on each new release. What we need to make that happen is the web team to provide that framework for the documentation and a documentation team to volunteer to do the work and write or modify the docs.
We just may not have the resources we need to make that happen. By the way have you looked at the
http://wiki.squeak.org/squeak and
https://squeak.org/documentation/ pages? There is a lot of really good documentation out there but it does take some digging and you probably will run into issues related to different versions. Much of it should still be relevant. If you run into issues we are here to help!
All the best,
Ron Teitelbaum