I was a little hasty in that answer
The short answer is, yes you do need to use iTunes with iPods. iPods were specifically designed to only work with iTunes. Yes, there are ways around it. Through hacking and/or third party software (ie Floola). I don't really have any experience with that because I've never bothered. I knew going in that iPods and iTunes were a closed ecosystem and I wasn't really interested in doing the hacking/third party software. If I didn't want to use iTunes, I would never have bought an iPod. I was using iTunes for about 6 months before I ever got an iPod. Fast forward a few years later, I own players that do not need iTunes that I use along side my iPods.
Buying from iTunes: I suggest you don't. If you ever want to have your purchased music playable on other players beside the iPod, don't buy from iTunes. Most of the music iTunes sells are DRM'ed.
What does DRM stand for? Digital Rights Management. Think of it like a lock. It locks in what you are able to do with the music you purchased. In the case of iTunes purchased music, you can put the music on 5 computers (back in the day, this would have been considered generous because other services only let you put them on 3). You can only put them on iPods. You can only burn the exact same playlist with the purchased songs to audio cd 5 times. Of course, you can get around those restrictions by burning them to audio cd then reripping them. DRM gone. iTunes does have part of its catalog DRM free. They are iTunes Plus tracks. They are not mp3s but unprotected AACs that are playable on any player that supports them. Examples of such players are the newer Sony players and the Creative Zen. Otherwise they can easily be converted to mp3 without doing the audio cd burn the rerip.
How do you know your WMA files have DRM? You indicated that you use Napster. If you bought from the Napster store at any point before May 20, 2008, they more than likely have DRM. That is the date that they officially went DRM-free for its entire catalog of 6 million songs. They may have started a slow rollout from the time it was announced in January '08 til then. And the format they are selling in is MP3 not WMA. If you have purchased tracks that are WMA, more than likely they are DRM'ed. How can you tell for sure? Go to the place on your hard drive where Napster puts your songs, but don't open the Napster software itself. Go to the artist/album/song that you know you purchased from Napster. Hover over the file and a box should pop up saying what kind of file it is (I'm using MS Vista). If it says something like "Windows Media Audio (protected)" then, BINGO! You have DRM. If it is an mp3, then no DRM. If you don't get the box, right click on the file and select "properties." Go to the details tab and you should be able to see the file type. CDs that you ripped would have no DRM and hopefully you ripped them as mp3s. DRM'ed WMA songs cannot be put on iPods without doing something to them first. While iTunes can convert UNPROTECTED WMAs (no DRM), it cannot convert ones with DRM. If you ripped your cds as MP3s, then you DON'T NEED TO CONVERT.
So, what to do with all thoses DRM'ed songs? You can do the burn to audio cd and then rerip to your computer. Then you'll probably have to fix the tagging information. What will probably happen is that when you rerip to your computer, the song titles may come out okay (or you could get track 1, track 2 etc), but you might have "various artists" under artist info and "compilation album" under album information. You can manually change this information, but if you have hundreds of songs this can be tedious. I believe there are programs that can help you with this, but I'm not familiar with them.
Another option is to repurchase the songs, either on Napster (since they are DRM free now) or another service that sells DRM free music. Why not iTunes? I've already answered that...because most of their songs still have DRM. I have many iPod and don't buy from iTunes anymore. I use Amazon's mp3 download store.
The last option is to ditch the iPod and buy a player that supports Napster's service.
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