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First off...I'm sorry. This isn't going to be super-simple or automated.
The Insignia MP3 players play MP3 and WMA audio files only (okay...and audio books). If you have a pretty nice collection of unprotected music files that you have purchased from iTunes, then you'll be able to do this conversion.
The Insignia player will not sync with iTunes...the program and the player are not compatable. You do not need to use Windows Media Player to load music on your Insignia player.
Here's the process:
Set your Insignia player to Mass Storage or "File & Folder". This makes it look like another drive to the computer.
Navigate to the Options or Preferences area (it's different depending on whether you use a Mac or a PC), select the BURN tab and set the file format to MP3 and the quality rating you desire (I suggest either 128kb or 192kb).
Select the songs you want to put on your player.
Tell iTunes to "Conver to MP3" the songs you have selected.
Once these files are copied as MP3s, Navigate to the iTunes folder (should be in My Documents/My Music/iTunes). I reccommend placing a shortcut to your iTunes folder on your desktop for future use.
Drag and Drop your music files to your Insignia player.
You're good to go. Unplug the Insignia player and enjoy!
Here is what is going on. All iTunes songs are in AAC format. The Insignia Pilot cannot read thos files, and the Rhapsody music service cannot read them either. You will need to redownload all of the songs that you want in Rhapsody itself. If you do not want to pay the monthly fees, then I would not download any songs from Rhapsody - they will cease to work after your Rhapsody subscription expires.
You have a couple of options. You could buy an AAC to Mp3 Converter software - this is not free, as far as I know - you also want to be careful, because some sites that advertise these products are scam artists - they don't let you try the product before buying.
Another option is to get Limewire or Morpheus - the free versions of thse services run extremely slow and give you a lot of ads, but they allow you to download Mp3 format songs for free without monthly fees.
Mp3 players just aren't as easy as they used to be.
You'll need to erase the internal and external memory, then re-add all your files.
You can use Windows Explorer to transfer files to your insignia sport player. First, in the settings on your player, go to Settings, USB Mode, Connection Type and select File & Folder. Then, plug your player in to your USB cable. Windows XP should automatically find your player and make a new drive letter in Windows Explorer. Simply drag and drop your files from your c drive to the new drive for your player. You'll notice that when you delete the files on your new drive for your player that it doesnt remove them from your player. You'll need to use your player (settings, system, erase internal) to erase internal (and external), but after that when you add new files, they will be added to the player when it does the profiling after you disconnect the USB cable. Dave@OgleServices.com
When using your media player... you need to first figure out if you are using windows media player 9 or windows media player 10. Also what windows are you using on your computer, that makes a difference as well... Make sure you have the mp3 player plugged in properly and then...Once you are in your windows media player go to your lib tab... soon as you are in there then on the right side there should be section on where you could build a lib list. Meaning you should be able to pick the songs in your lib and just drag them over. On the bottom you should see something that says sync... Once you've choose your songs and dragged them over... all you should have to do is press the sync button and it will do all the work for you from there. And it should let you know when its complete...mine does. Hope I could help you.