If you want to use OSS from the start, you can use python and
wxWindows and keep some of the modules you write when porting to
Plone.
I definately agree that code reuse is the way to go.
One other option (other than wxWindows) is PyGTK/libglade. It won't
have the exact same look and feel as most windows programs (because it
doesn't use native controls), but you get to build your GUI in Glade
which is a pretty easy to use gui builder and with that you get the
advantage of more natural separation between core program logic and user
interface code. I think wxWindows may have a gui builder, too, but I
think it may be worth the effort to check both out.
Btw, with either option you get portability to Linux for free.
--Ray