The fourth "automate other windows apps" app I tried, VistaTask, passed the "can control notepad" test with flying colors! A free trial is available at http://www.vista-software.com/
I don't know how close that tool is to being useful for software testing -- it's not specifically aimed at it -- but it's nice to see at least one such app actually working on Wine.
Again, kudos to the Wine developers for getting Wine to this point! - Dan
-- Wine for Windows ISVs: http://kegel.com/wine/isv