I am on a Mac, and I can connect the phone in Mass Storage mode, meaning that it shows up like a USB drive. What's the easiest way to get my iTunes music and podcasts onto the phone?
I'm also open to suggestions of other good media players that sync easily with USB drives.
Some of the solutions provided below ( like edwardclint's suggestion to use Sailing ) appear excellent. However, if you want direct, customizable ( even scriptable ) control of what you sync to your phone, you could always use Rsync to synchronize your desired content.
Rsync is a free UNIX utility included within the BSD core of your operating system. If you would like to try this method, simply follow these steps:
1) Open the Terminal application within your Utilities folder.
2) Use the following command structure, as displayed below, to synchronize the folders between your Mac and phone:
rsync -alE --delete --ignore-errors --update --progress /< path to your iTunes Music folder >/ /< path to your phone's music folder >
Example: rsync -alE --delete --ignore-errors --update --progress /Users/yourusername/Music/iTunes/iTunes\ Music/ /CompletePathToYourPhonesMusicFolder
Then press the 'return' key. Depending on the size of your music library and speed of the connection to your computer, it may take some time to complete, but it will give you continual status of the copying process within the terminal window. If you encounter permissions errors during the process, try again, only this time pre-pend 'sudo ' to the front of your rsync command. Be careful though, as entering typo's while using 'sudo' can prove disastrous. It's not that the command itself is dangerous -- it's just the fact that your computer will do exactly what you tell it to do with superuser privileges and no warnings when you use sudo. If you accidentally tell it to erase something critical ( because of a typo or otherwise ), your computer will dutifully do that and you will likely be re-installing your software and/or personal data to fix your typo. Just saying...
Once the rsync has completed, any future rsync's will go much faster, as it will only transfer the data ( or songs ) that have been added since your last sync. It will also automatically delete any songs on your phone that are not present within your iTunes Music folder so that both folders should remain perfectly sync'ed.
In addition, you can synchronize any folder you like with the rsync command. It could be a subfolder within your music folder, any number of subfolders, or just a single song if you so choose. You can also use it to synchronize notes, pictures or other files with your phone. All that's needed is to follow the command structure listed above and include the full paths to each folder you desire to sync between your phone and your computer. You can also bundle the individual rsync commands into a script that can be easily launched by an alias on your desktop, automatically triggered by a system event ( like mounting your phone's mass storage drive ), or whatever you specify. That's the beauty of making use of the UNIX layer within your operating system -- it affords you an unusually high degree of flexibility in how you go about your desired tasks.
QUOTE FROM HERE http://www.mahalo.com/answers/software/how-can-i-sync-itunes-to-my-nokia-n900