I am can't seem to figure out how to make diddles sound like diddles in Finale 2004 with the articulation tool. Accents work fine but diddled notes don't play back any differently. Any help would be appreciated.

Check out the "TG Tools" option for "smart playback." You should see this in your plugin's menu. I'm not sure if this is the same in Finale 2004, but I know that's how it was done in Finale 2002-3.