Have you tried the smiley plugin for Windows Live Writer? It makes adding smileys or other tiny graphics to your blog entries so quick and easy. This is by far my favorite plugin.
The fabulous part of this little plugin is that you can add custom smileys, your favorites, or delete the ones that you know you'll never use. Though I wish I could rename the tabs so that I could use one for say, weather icons, or mood icons, it is a wonderfully functioning plugin. Here are two great places for mini smileys and icons. Free Icons Web and Free Icons Download. Have fun and go crazy!