We just installed an updated version of the image gallery module that makes uploading work seamlessly when you are writing your content in our WYSIWYG editor. See our instructions to upload a photo or an image while you're writing.

Also, we added the ability to place a random image on your sidebar that shows the thumbnail (i.e. a smaller version) of a photo or image added to your gallery. We've added instructions on how to add that block to our documentation on configuring the image galleries on your site.