Q: Now that iTunes has FINALLY become , I am looking to try out a different type of MP3 player. I have been stuck to iTunes because I have a couple thousand purchased songs, and I really like the setup and use of iTunes overall. I have always wanted to try a different MP3 player. Now that I can, can you tell me what you think is the number-one-sounding MP3 player that you have tested?--Mark, via e-mail
A: There are a couple of things you will want to keep in mind in your situation. The first is that the files that you have already purchased through iTunes are still going to be protected AAC--and only compatible with the iPod--unless you choose the upgrade option in iTunes. This will replace the DRM-protected tracks with DRM-free versions at a cost of . Next, any music you continue to purchase through iTunes is going to be in AAC format, which is not as universal as MP3. As such, you'll want a player that supports the format, which is not so hard to come by nowadays. Finally, you said you really like the iTunes interface, so if you want to continue using it, you'll need to find a way to integrate the new player into that jukebox, which is optimized to only work with the iPod.
So first things first: get iTunes to work with non-iPod MP3 players. Try a software program like iTunes Sync or iTunes Agent. Either app should do the trick, although you're going to get a better experience with your player if you use a jukebox that is meant to work with it. Almost all non-iPod MP3 players (with the exception of the Zune) work well with pretty much any Windows jukebox: Windows Media Player, Media Monkey, Napster, Rhapsody, WinAmp, etc.
Once you've gotten that taken care of, it's time to talk players. My two top candidates for sound quality are the Sony S-Series Walkman and the Samsung P2, which both also happen to support AAC audio. (You may want to note, however, that the P2 is about to be replaced by the .) The Sony E-Series Walkman also offers comparable audio quality and support for AAC.
MP3 Mailbox Monday is a recurring feature where I answer a selection of questions about MP3 players and accessories, such as headphones, speakers, and music services and software. Check back often to see if the advice presented here might be of some use to you, or send your questions directly to me. (Note: We never include last names, but if you prefer to remain completely anonymous, please state as much in your e-mail.)