Based on suggestions from Allan I've revised the Fetch Categories command to work with a multi-select menu (using osascript). You can now just choose multiple categories at once and it will insert the text "Category: your_category" for each selected item. Once again, this is only tested with Wordpress on my end, so I'm curious to hear if it works with other blogging software.
I have also made the command available for download at: http://blog.circlesixdesign.com/downloads/FetchCategories2.zip
I'm having a lot of fun writing commands and snippets, but I'm no programmer. If anyone sees fit to clean up the code, feel free, and I'd love a copy to learn from if you do.
Brett