To fill the shuffle with the latest podcasts based on what I discovered and posted previously:
1. Create a Podcast play list
2. Select all of or just the desired podcasts in the Podcasts Library (that is the list of iTunes Source/Playlists on the left). You don’t have to expand any of the podcasts to reveal individual programs.
3. Drag the selected podcasts into your newly created Podcast play list iTunes Main Library.
Note, If this is done multiple times, podcasts are only copied once, that is, there are no multiple items in the Podcast play list.
4. Create a smart playlist called “New Podcasts”. It will Match all of the following conditions:
4a. Genre is Podcast
4b. Play Count is 0
4c. Live updating checked
4d. Setting Limit and matching only checked songs is up to you.
5. Copy the contents of the New Podcasts play list into the iPod Shuffle.
Subsequently, filling your iPod Shuffle is a two step process.
1. Select the podcasts in the Podcast library and drag the selected items into the Podcast play list iTunes Main Library.
2. Drag the desired new podcasts from the New Podcast play list into iPod Shuffle.
Now, we could replace step 2 by using the iPod Shuffle auto fill button which should work, but I have yet to get this feature to work correctly. I suspect it may because I use my shuffle as a flash drive. I need to play with that some more.