I have now downloaded, installed, used, and paid for the Salling Media Sync mentioned above. It works great on the Mac and I understand that they have a Windows version to. Give it a spin:
1. Plug your T-Mobile G1 into your computer using the supplied USB cable.
2. It should appear as a mass media storage device on your desktop. Mine was named "NO NAME." If it doesn't appear, go into the Settings app in Android on your phone, choose "SD card & phone storage," and then make sure there's a green checkmark next to "Use for USB storage."
3. Download the free trial of Salling Media Sync:
http://www.salling.com/MediaSync/mac/
3. Install it.
4. It launches and immediately finds and parses your iTunes playlists, including podcasts. There were a couple of quirks in which podcast feeds were listed twice under slightly different names, but that was a minor problem.
5. In a settings screen that is very similar to the one in iTunes itself, choose which and how many podcasts to update.
6. Click sync. The syncing speed is pretty good, but not as good as an iPod, probably due to the slower speed of the microSD card.
7. When done, unmount the phone's drive "NO NAME" from your desktop.
8. Go back into Android's Settings app and deselect "Use for USB storage."
9. Go to the Music app and play your tunes or podcasts.
A few notes:
-- As mentioned elsewhere, you cannot play media from your internal microSD card while it is mounted on your computer's desktop. This is likely a limit of the underlying technology, not of the phone. iPods behave exactly the same way.
However, there is one thing that is likely a limitation of the phone: even after you unmount the phone's microSD storage from your desktop, you still HAVE to go back into the settings and deselect "Use for USB storage." Only then can you play music and movies.
--Album art is transferred with the files.
--Unfortunately, music and podcasts are intermingled in your lists. There seems to be no way to view only the podcasts. Even making a playlist containing podcasts and trying to sync them as music doesn't work. I'm not sure where the fault lies here--I've had similar difficulties with iPod Shuffles. The problem is compounded by the lack of a "genre" view in the music player app.
As I primarily listen to podcasts, and not music, I will likely only have music on it, for now, but it is something that needs a solution. A "genre" view alone would do it.
--I have not yet tried it for video podcasts.
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