Regarding the web infrastructure, do you know Midgard (www.midgard-project.org). I don't suggest to use that tool, but I like the site layout and the ideas behind that tool. So I recommend to check it out. It's similar to ZOPE (www.zope.org) in its ideas and a free, opensourced web site application builder with an easy to use interface, built upon apache, php and mysql.
If we could create something like this for Squeak, that would be great :-)
bye