Live Writer is definitely best windows tool for blogging. But as well as many other ms products it has some bugs which with non-transparent behavior annoy some people.
So I have 2 problems with Live Writer.
Install failed
With release of version 2008 you must install LiveWriter from united Live installer - which downloads needed software during installation. And on my home PC it says failed without any additional information.
Workaround for problem - download installer, that contains writer - from here:
Just select writer.
(400) Bad Request when upload post with images in blogger
The problem appears when post image through clipboard or in .png for example. So workaround - save images to disk in .jpg before add it to draft.
more about - here
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