Well brother, I tell you what... I have a little program called JHymn that you simply must try to find... Im not sure if I can say more or not but a search engine will help you do the rest!
The iPod is first and foremost an MP3 player. The iTunes application makes a nice interface for syncing your iPod to your music library or any part of it. iTunes also carries the iTunes music store which allows you to purchase encrypted music. If you buy music from the iTunes store, the encrypted files will only play on authorized computers through iTunes or the QuickTime player (up to 5 of your computers) or your iPod(s).
You can rip CDs to MP3 with iTunes 'til you're blue in the face and load your iPod or whatever else. If you rip CDs, there's no encryption. If you have encrypted music in iTunes, you can burn a standard music CD from a playlist and the music is then an unencrypted, play anywhere CD. You can also load non-iPod players from these ripped CDs with a different audio format.
You can play music files directly on your computer without iTunes. Just find the files and play them. If the file is encrypted, the player will detect if it's on an authorized computer and play it without question. If the file is NOT on an authorized computer, it will challenge the user for the password for the files and not give up until you put in the password. If you've already authorized your 5 computers, the password will not work (it phones home to check).
You'll hear a lot of FUD and anger that Apple's audio file format won't play on a bunch of other players. The format Apple prefers is called AAC and is a world standard, unlike WMV from Microsoft which is proprietary. Apple licensed AAC which is also known as Dolby Digital, MPEG4, AC3 and a few other things. This audio format is used on all DVD Videos including the upcoming Blu-Ray and HD-DVD formats, so it is truly universal and may well outlast the WMV format. There should be no fears of recording AAC formatted audio.
I am fearful of the proprietary FairPlay DRM system applied to iTunes music. However, it's easily stripped by buring a CD from your files, but the original music file may not play if FairPlay is ever forgotten or replaced. Burn a CD and re-rip it to unencrypted AAC or MP3 if you want.
The reason other players don't carry AAC decoders is the license they agreed to with Microsoft forbidding the inclusion of a competing audio format (except MP3) if the player has WMV. Microsoft almost wanted to kill MP3 for that reason and replace it with WMV, but the backlash from consumers would have been very damaging. They will allow MP3 until WMV has reached critical mass, if it ever does. The manufacturer's hands are tied because Apple will not license their FairPlay DRM in order to protect iPod sales, so the [almost] only other option is to hook up with a willing Microsoft and hope they can overpower the iPod.
Everyone's anger should be directed toward Microsoft for preventing you from having a universal player. Of course if Microsoft didn't do that, every other player would be able to play at least unencrypted AAC and WMV may fall away as a viable audio alternative.
Microsoft is trying very hard to broaden adoption of WMV so that, one day, they will be able to dictate the terms of listening to music in that format. It's how they managed to own all they do and they'll continue that practice for the forseeable future. The technical landscape is littered with technologies they've killed in that manner.
you should check out anapod explorer. Its at http://redchairsoftware.com I have used it for over a year and it is very simple to use and is windows based.