9-9-10 update: doubleTwist is the current king. See end of this post for more info.
The bad news is that my new Droid Incredible doesn’t read .xml or .asx playlists, only .m3u. So while it’s relatively easily to sync music to the device (Windows Media Player does it natively, iTunes requires a little program called iTunes Agent), getting playlists to sync is a bit trickier.
You can get Windows Media Player to save playlists as .m3u, but it really wants to save as .asx or .wpl, so it’s a pretty serious pain in the butt (you have to actually “save as” the playlist, and then you have the original .wpl AND the new .m3u in your library, and making sure you then delete the right one is a pain, blah, blah, blah…). [update: Unfortunately when Windows Media Player syncs with your device, it saves the playlist on your device as an .asx, so it’s no good for Android devices. I found this out after a LOT of messing around with exporting my iTunes playlists to WMP via MusicBridge and then saving each .wpl list as an .m3u and then deleting the previous .wpl… only to have the files converted to (unusable) .asx files once WMP synced with my Droid. There doesn’t seem to be any way around this. Even changing the .asx playlist to an .m3u playlist on your device doesn’t matter –it will be re-created as an .asx file on your next WMP sync (the .m3u list on the device won’t be updated –a new .asx is created). Annoying to say the least.]
There is a program called The Missing Sync that is just what it says, the missing sync software that SHOULD come with your Android device (what the hell Android/HTC?). It supposedly syncs texts, contacts, photos, video, music, playlists, ringtones, call history, etc. However, I’m not willing to drop $39.95 to try it out, especially when the Incredible isn’t specifically listed as a supported device on their website (the Moto Droid is the newest device listed). [update: The Incredible is supported, and my review of The Missing Sync is here.]
I used iTunes Agent for a couple of minutes, but then realized it will only sync music (not playlists). iTunes Agent is a little program that sits in your tray constantly monitoring for iTunes. It places a folder for your device in the iTunes playlists, and when you hook up your device it syncs all songs in that folder to your device. However, like I said, there is NO support for playlists. The author has been promising playlist support in version 2.0 for some years now, but considering how long he’s been promising this, I don’t see it happening anytime soon.
THIS IS THE ANSWER TO YOUR QUESTION: There is another program called iTunes Export by Eric Daugherty that does the trick for me. Simply install the program and use the GUI version (unless you’re really into command lines) and then select your library location, select the playlist(s) you want to sync, set your output directory to the music directory on your device (SD card or phone memory), select “include UTF-8 BOM” (or it won’t work), select “copy iTunes Structure” (so files sync into folders that are identical to your music library, the “author – album” structure), and you’re golden! Just remember to run iTunes Export after you’ve made any changes to your iTunes playlists. It’s a bit of a pain having to run a separate program to get your playlists to sync after any changes you make in iTunes, but this is the best workaround I’ve found.
doubleTwist is another program getting some attention, but it’s Moto Droid support is only in Beta, and there doesn’t seem to be Incredible support yet (they do support the Palm Pre though, for those of you looking for the elusive link between iTunes and the Pre).
9-9-10 update: doubleTwist is the current king. With recent updates, you simply install the desktop app, click “iTunes” to import playlists, and off you go!!! It will also convert an video to the proper format for your phone. Just drag any video file into the app and it’ll convert for you. I’ll likely do a review soon.