The plugin still has a problem with duplicate filenames, as reported by wely a year ago. Here’s a good summary of the problem: http://wordpress.org/support/topic/how-to-automatically-change-file-name-when-publishing-file?replies=2
This bug is a show stopper when Live Writer is used as a blogging tool, as it uses “image.png” as the file name for all the images which are added from the clipboard. Live Writer will upload all the images using the same filename and the plugin will just overwrite the previous image.
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