Hi hawgwild, is this on the Windows XP computer that you installed the Blender onto? We haven't seen this problem before and would be interested to figure out what is causing it.
If I understand correctly, you have created multiple workouts in the left column in the Blender, then pressed the "Create Workout" button for each, it creates video files with different names in the Videos folder, but when you drag these multiple files into iTunes, they are all reading in as "Workout #1"? If you could please confirm this I will pass on the information to our lead developers. Thank you!