iTunes + iPod Setup

These are the settings I use to listen to Podcasts efficiently with iTunes.

Podcasts set up

First off, I subscribe to a bunch of podcasts in iTunes. I make the default settings for podcasts download the most recent one and keep all unplayed episodes. For some really active podcasts, I have the download option set to do nothing, and then I download the episodes I want by hand.

Podcast playlist set up

Basic setup

Next, I create a smart playlist that searches for all items with Media Kind of "Podcast" and play count of 0. With this set up, new podcasts (if set to download the latest episode) will automatically appear at the end of this playlist and old podcasts will disappear as soon as they finish playing. iTunes will eventually delete the played podcasts automatically as well (if "episodes to keep" is set to all unplayed episodes).

I like the above set up. You don't have to worry about managing the podcast files at all (except for choosing episodes to download from podcasts that you don't have set to automatically download the latest episode).

Adding non-podcast files to playlist

Sometimes I need to add non-podcast files to the podcast playlist (like podcasts that are not posted to iTunes and have to be downloaded manually). To do this, I open the file in iTunes and then right-click on it (in iTunes) and choose Get Info->Options and set the Media Kind to Podcast. Doing this causes the file to disappear from the "Music" section of iTunes and to appear in the Podcast smart playlist. It can now be sync'ed to the iPod normally. After it is played, it will disappear from the playlist though. To make sure that it is really removed from iTunes, I create another smart playlist called "ZAllPodcast" (the "Z" is there to make the playlist be on the bottom of the list since I never listen to this playlist) that includes all files with Media Kind = Podcast and no other conditions. The played podcast will still appear here. To delete from iTunes, select it and then do Option+Delete. You also have to delete the audio file by hand.

iPod sync set up

For music, I choose to sync only selected playlists, artists, albums, and genres because I have a large music library. For podcasts (and iTunesU), I sync all unplayed episodes of all podcasts.

Syncing the iPod

This is the tricky part. I have an AppleScript called SmartIpodSync.scpt that I use to eject the iPod. Here are the steps of the script (the script is available at https://github.com/willsALMANJ/applescripts):

1. Check for iPods and exit if none are found. Otherwise perform the following steps for each iPod.
2. Check that UIScripting is enabled in System Preferences and show a message explaining how to enable it if it is not. (This is necessary because the script needs to set several properties not exposed to AppleScript and interacts with them by telling iTunes which UI elements to click on).
3. Find all played podcasts and tell both iTunes and Finder to delete them. This is done in case podcasts were downloaded and listened to on the computer but not yet cleaned out by iTunes. By deleting these podcasts now, iTunes will not waste time sync'ing them to the iPod later.
4. Using UIScripting, turn off live updating of all smart playlists sync'ed to the iPod. This step is necessary because when iTunes sync's a smart playlist with live updating on the playlist appears in the iPod with an unexpected ordering (maybe date downloaded?). I like to actively keep rearranging my podcasts by hand and then just always play the top one on the playlist (which disappears as soon as it is played). That way stuff floats to the top as I listen (since I mostly listen chronologically with small tweaks).
5. Sync the iPod. Using UIScripting, monitor the text of the status window at the top of iTunes for "iPod sync is complete." and allow the script to continue once this text appears. This waiting loop allows the iPod to sync before continuing the script without waiting extra time.
6. Eject the iPod from iTunes.
7. Using UIScripting, go back through the smart playlists that were sync'ed and turn live updating back on so that new podcasts (and songs for other playlists) will be added automatically.
8. Tell Finder to hide iTunes (set visible of process "iTunes" to false).