After many failed attempts at building webkit I was finally able to get all the pieces together and build and debug webkit under visual studio. I can now start playing with the live system, rather than browsing through the code.
The big problem I faced was the builds failing because the line endings used in the script files were set to CRLF whereas I had setup my cygwin to use unix line endings. I was able to use Notepad++ to fix them and finally get a working build from the latest source. Another issue I faced was that using subversion from within cygwin was very error prone and always left the working copy in some errorneous state, using tortoise svn directly from windows helped here.
So far the webkit code base looks a lot better organized than the mozilla code base so hoping that I can learn and contribute back to this project.