I posted this originally on our sites blog, but considering how many emails i get on this topic, i thought i would post it here.
Original Blog Post with images BTW This is 100% legal, you aren't breaking any law or violating iTunes' TOS.
A common question that we receive is if MP4 players, the type we sell, can they work with music downloaded off iTunes. The answer is Yes and No.
Lets start with the NO first, iTunes was designed to work specifically with iPods, therefore the music was encoded in a special music format making them only work in iTunes and on iPods, however in early 2007 Apple announced that some of its music offerings would not be restricted to being used on iPods.
Now for the Yes, iTunes now has a special section called iTunes Plus, this is where they carry their non Digital Rights Managed (DRM FREE) music, but the price of one of these downloads is $1.29, as opposed to $0.99 if you download them with DRM.
How to download and convert DRM music from iTunes, this method will also preseve the ID3 tags such as artist name, song name, album name etc:
First you will need the latest version of iTunes from Apples website. You will also need a iTunes account enabled for iTunes plus - if you are signing up for the first time, you will be prompted for this option, if you already have a iTunes account then you will be prompted to enable iTunes plus when you first select iTunes Plus from the menu.
Once in iTunes Plus, find a song(s) you want and download them, then goto your music library select the songs you want converted then do the following:
1. Goto Edit > Preferences
2. Click on the Advanced Tab, then select ‘Import’, under ‘Import Using’, choose MP4 Encoder. Then under ‘Settings’ select the audio quality you want - if you want higher than 192kbps then select custom and set your own KBPS for the outputted file.
You may get a message saying you do not have high enough permission level - ignore it.
3. Select the songs you want, then right click and choose ‘Convert Selection to MP3′ this will then start to convert all the files you selected to MP3, don’t worry, your original downloaded files won’t be deleted. Once the conversion is done you will see duplicate files of each song.
4. The converted files will be in your iTunes music folder, just copy the converted MP3 files to your MP4 player and your done!
The entire process is not long, the conversion process is fast and easy, depending on what type of player you have you can either use your regular directory explorer to copy files or use iTunes or Windows media to sync your music files to your player. This method does retain your ID3 tags.