I just want to report you that etoys has just been accepted in the non-free branch of Debian. The reason to put it in non-free (even if I (we) consider it's free) is that we want to give the chance to the Debian users to use it while the discussion on moving it to main continues. The next step is filling a bug against ftp.debian.org saying that etoys in non-free is an error, as it's a free package.
From my point of view, the main obstacle for Debian is the fact of not being able to bootstrap, rebuild or check the changes in the image using plain text files. Some of the things that have been said in this thread might head to implement a way to demonstrate that this is possible, I guess that it will be possible with future images, not with the current one. Obviously, all the help or participation from the Squeak community to achieve this goal is very welcome. Also, if some of you would like to help to maintain Squeak in Debian, please, tell it, so we can consider creating an alioth project in Debian to maintain this image and future squeak images in the distribution.
As Bert previously mentioned, Debian is not only for Debian users, but also a seed for other distributions like mepis, knoppix, linex, skolelinux, ubuntu, etc. that use its repositories and packages, so having Squeak in Debian is a warranty to make its spreading and use easier for these distributions users.
Regards. José L