Let's face it, Windows Media sucks. Really bad. It's an awful program to use.
And while iTunes has it's fair share of problems, it's still infinitely better than Windows Media.
The biggest problems iTunes faces are the same problems all Mac devices face: Mac keeps an iron grip on EVERYTHING. But as usually, people have figured out ways to pry open Apple's greedy little fingers.
I had been manually moving tunes back and forth from my computer to my Omnia. Playlists are simply XML files, and all the songs are just MP3's. It seemed like it would be easy enough to write a program to automate generating/converting/moving files... and sure enough, somebody's done it (sort of)!
There are a couple of pay programs, but me, being the cheap bastard that I am, found a great free one called iTunes Sync (creative, no?) from Binary Fortress (these guys also make a really great multi-monitor display program called Display Fusion).
I installed and set up iTuneSync according to the very simple instructions on the BinaryFortress website. I created a folder in iTunes called "Omnia Storage Card" and filled it with other play lists. I changed my USB connection for my Omnia from ActiveSync to Mass Storage Device. I clicked "Synchronize MP3 Player" in iTunes Sync, and voila! Everything in the "Omnia Storage Card" folder was synced to my Omnia.
Oh, glorious day!
One caveat I've realized after actually spending some time with this... the program only syncs the files... no playlists are transferred to your device, so you still have to manually sync (see problems below) or create playlists from within Windows Media Player Mobile. The developer of iTunes Sync is promising multiple playlist syncing in the next version, but he is not promising any specific release date for the new version.
So for now, this solution is only good for syncing the songs that you have in playlists. You will still have to manually create the play lists themselves. A workaround would be a program that could convert iTunes XML play lists to .ASX, which is the format Media Player Mobile uses.
Eric Daugherty created a program that will convert iTunes XML playlists to m3u, ext, wpl, or zpl (it will also transfer the actual MP3 files used by the playlist, which is GREAT), but apparently Windows Media Mobile will not play any of these formats (go figure). So what I need is a program that will convert the iTunes XML files to .ASX (which is used by the Windows Media Mobile player).
There are plenty of players for Windows Mobile that will play M3u, so I guess I'll just be using a different media player for now (pay attention Microsoft).
[Oct. 4, 2009 - UPDATE] While Windows Media Player mobile can't use .WPL files, Window Media Player 11 does... so the solution is to use Eric Daugherty's export program to create a playlist from iTunes for Windows Media, and then simply use Windows Media (via Active Sync) to place the iTunes playlist (and files) on your Windows Mobile device. If you have Eric's program set to generate the WPL file and place it in your Windows Media Music directory, it will simply appear under playlists in Windows Media, and you can sync with your device from there.
Woo-hoo! Not as elegant as I'd like (you have to use three programs), but it works perfectly!
[ANOTHER SOLUTION] Music Bridge will sync iTunes and Windows Media libraries. It's a pretty robust program with many options as to what you can sync (see the download page for a description). After running music bridge, you can then sync your device using Windows Media/ActiveSync as above. When I tried this method, it didn't seem like the sync was working (the iTunes lists didn't show up under playlists in WinMedia). However, under the sync settings in Windows Media, all the iTunes playlists were available for syncing with my device. Weird, but it works!
So hopefully one of the above solutions will work for you!
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