I will tell you folks that even though Live Writer has been around for years now, I am surprised there aren’t more extensions for the software. One of my biggest problems is that Live Writer still doesn’t yet support a "Featured Image" setting which can easily allow you to post your blog post and set the featured image from within Live Writer, this is one of the "MUST HAVE" extensions for Live Writer that somebody needs to install.
When running a blog where the featured image is a priority to set you have only two options, letting WordPress set the featured image as the first image found in the blog post, or manually editing your post in WordPress Admin to set the featured image after you Post it as a draft to your blog.
I would have preferred not to have to manually set a featured image, but there is no other option I have been able to find at this point from browsing the WordPress Plugins or Live Writer Extensions area. I checked on Google and couldn’t find anyone who developed a solution to this irritating problem either yet.
Let me know if you use Live Writer and have to work around the issue where Live Writer cannot set a featured image for your blog posts, or if this issue isn’t one that you face.
That being said, Windows Live Writer is still one of the most efficient blog authoring software components out there and it is completely free. I highly endorse it and did a YouTube video showing how to use Live Writer as your WordPress blog post and page editor.