I am an admitted fan of Windows Live Writer. I think it is an excellent tool to use for writing blog posts. I am always happy to try to answer questions people have about the tool.
When I am unable to answer these questions myself, I turn to the Windows Live Writer Group on MSN Groups. This is an excellent resource to use when you have questions. There is a list a discussions that you can search through. Many times you will find that your question has already been answered, if not just post your question and wait for the reply.
You will need an .NET passport to access the site. Once you have a .NET passport you will be able to join this group.
I used Windows Live Writer Groups when I was unable to embed video using WLW for WordPress. In the end, Scøtt of Scottisafooldev created the insert Video plug-in for WLW that I tested and have used, and it works great.
If you have questions about WLW, the Windows Live Writer MSN Group is an excellent resource for finding answers to these questions.