Back in 2008 I created and published a Smalltalk binding for the
free Haru PDF library. With the package it is fairly easy to generate PDF documents from Squeak and Pharo.
The code is available at http://squeaksource.com/HPDF.html
It is also mentioned on the seaside website as one
alternative for Smalltalk PDF generation (beside others).
It looks like Georg's company now had the same idea to wrap
this library, they created a new product called PDFPrinter.
Looks like they have a deeper integration into the VisualWorks
printing system for their customers.
However - generating a PDF programatically is still a lot of work. What is still missing in Smalltalk is a counterpart to Java's JasperReport or BIRT with a more WYSIWYG editor like systems and PDF creation by mixing templates with data...