Wow! Now I remember why I gave up on Win32 so long ago. I was in pretty much you exact position 5 years ago. After running into so many "gotchas" (I had a different word for them), I decided to cut my losses. I switched to Python and haven't looked back.
I won't start a holy war thread here, but you may want to carefully consider exactly what you want to do, and then compare your available language options before committing.
I would also like to highly recommend "How to Think Like a Computer Scientist" by Allen Downey. You can download it for free at
http://www.greenteapress.com/thinkpython/
Allen Downey is a prof at Olin College (my alma mater). Several years ago he wrote a Java version of the book and copy-lefted it. Someone took the book, revised it for Python, and rereleased it. Allen then read this book and learned Python.
... Yes, he learned Python by reading his own book!
It has some chapters that deal with a little bit of user interfacing, so it shouldn't be hard at all to get going.
Good luck!
Eric