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Itunes2DROID?

I have tried a few. The easiest one for me was Salling Media Sync.
Salling Software - Salling Media Sync for Windows

However, the free version recopies the playlist files every time you sync. The paid version uses the "smart" feature and just makes changes. I never ponied up for the paid version, it's a little steep at 22 bucks. Salling Free works well, just slow, and doesn't try and "replace" itunes like Moto Media Link does.

People have said good things about itunes agent, also free, but I never quite got it to work right. And if you set the sync up wrong, it has the ability to delete all the music from your PC.

Edit: I tried double twist as well, but the re indexing on every start killed it for me.
 
I have tried a few. The easiest one for me was Salling Media Sync.
Salling Software - Salling Media Sync for Windows

However, the free version recopies the playlist files every time you sync. The paid version uses the "smart" feature and just makes changes. I never ponied up for the paid version, it's a little steep at 22 bucks. Salling Free works well, just slow, and doesn't try and "replace" itunes like Moto Media Link does.

People have said good things about itunes agent, also free, but I never quite got it to work right. And if you set the sync up wrong, it has the ability to delete all the music from your PC.

Edit: I tried double twist as well, but the re indexing on every start killed it for me.

Motorola Media Link doesn't try to replace iTunes. You can set it up so that your iTunes playlists are automatically synced to the droid, that is how mine is set up, and all I need to do is put a song in the playlist in iTunes, and it will be automatically synced to the droid when I plug it in. That is not to say that you couldn't replace iTunes with MML, but why would you want to.
 
Doubletwist works fine for music/itunes playlists. it sucks for video though, takes forever then puts everything out of sync, at least on a Mac which Doubletwist was originally built for.
 
ITunes my walk man is the only program you need. Gave my iPod touch away because the syncing is exactly the same. Plug in the Droid and it syncs with iTunes.
 
Please explain this in a little more detail. Is there an app that you are referring to?

Sorry for not going into more detail. After looking, this is for Mac's only (but Im guessing there has to be a Windows equivalent somewhere).

Downloads - itmw - Project Hosting on Google Code

Anyway, you mount your phone onto your computer, take iPodMyWalkMan, show it where your Music folder is located and then choose a playlist. Everytime you connect your phone, ITMW detects the phone, starts itunes and syncs your library or whatever playlist you choose to the music folder on your Droid. Like I said, I gave my wife my ipod Touch because there was literally no difference as far as syncing goes anymore. Just plug it in, let it sync, pull it out. It even un-mounts your phone after its done syncing.
 
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