So, after debating at length with Göran about pros and cons of Smalltalk as a platform for real world development, I came to the conclusion that Smalltalk was worth looking into in greater detail, and since I’ve been wanting to write my own blog/wiki hybrid, it was suggested that I check out Seaside, a Smalltalk-based framework for web development comparable to ASP.NET or Java Server Faces.
At first look, Seaside doesn’t look much different than ASP.NET. It’s all about modelling your application’s interface in terms of objects and methods (”messages” for you Smalltalkers). Pages are built up of components, inheriting from System.Web.UI.Control (ASP.Net) or WAComponent (Seaside) that can include other components. When the user does things with any component, it results in events being fired (ASP.NET) or messages being sent (Seaside). Both frameworks seem to strive to abstract away the request/response nature of the web, and to allow the programmer to use a more event-driven approach to developement. In addition, seaside uses at it uses continuations to make it possible to, for example, ask the user something (similar to how a modal dialog would do it in a normal GUI enviroment), and then do something with the provided answer — all within the context of a
method.
The main difference is that programming in the Seaside framework results in a lot less housekeeping code. The object is really a ordinary object, except that it’s executed through the web. The difference didn’t really dawn on me before I tried to recreate WACounter as a ASP.Net Server component — it did involve a whole lot of code to handle events, manage viewstate and so on.
From a security perspective, Seaside has problems with the fact that the session id is present in the URL, and it seems harder to make applications RESTful, but apart from those issues, Seaside is definitly a framework worth looking closer at. From my own perspective, I hope that the ASP.NET developers do 
Unfortunately, things elsewhere has been chaotic (and not in a good way), so I have not had any further time for experimentation with Seaside. As always, further progress will be reported here.
Update: This is a much better explaination of what continuation-based, or synchronous, web programming is.