Community Server Gallery
Although Windows Live Writer can work with Community Server out of the box (How to configure Windows Live Writer for Community Server?), direct uploading of 
images used in your post to the Community Server Galleries isn’t possible.
At least not out of the box.
Thanks to a new plugin for Windows Live Writer it is possible however.
After you download the file and extract it, the plugin needs to be manually installed 
(How to manually install a Windows Live Writer plugin?).
Once installed you only need to configure the plugin with your Community Server details.
With that in place you’re now ready to start posting as well as uploading images to your Community Server galleries.
Using the plugin you can browse the albums in your gallery. The programmer even added an “All Albums” option.
Download page for Community Server Gallery plugin for Windows Live Writer.
