Question:
Some artists show up multiple times on my iPod. What gives?
Answer:
Recent versions of iTunes allow to create sorting fields for tracks. If you put different values in the same sorting fields of tracks that belong to the same album, you'll see their corresponding artists showing up multiple times on your iPod. If you add another album of the same artist, you'll get yet another entry of the same artist.
Solution:
Use "Tools->Remove Sorting Fields" or "Tools->Create Sorting Fields" to remove/recreate appropriate sorting fields. Note that JakPod ignores certain words when sorting the tracks. These are configurable in "File->Options->iPod".