I'm a happy Mac user, but my roommate is adamantly pro-Windows. He works in tech support, likes gaming, etc. Anyway, about 10 years too late, he's starting to digitize his music collection. He still doesn't have an MP3 player (and when he does, it won't be an iPod), but he's got a pretty significant digital music collection now. He thinks that he's happy with Winamp (aren't I smarmy?), but having pilfered from his shared music folders, I know he'd benefit from a true library program. I could never get him to try iTunes, and apparently he's tried WMP and wasn't impressed. (He has an XP machine.) Are there any other alternatives I could politely suggest for him? I've been removed from the Windows world for so long, I don't know what's out there. I tried some Google searches, but didn't find much except WMP, Real (which at least used to be major bloatware), and WinAmp. If there's isn't an Open Source project for media management software, there should be. I know this post is antithetical for an Apple rumors site, but these forums have consistently been the most helpful to me over the years. It's not a huge stretch to say that this site influenced me to finally switch! Thanks in advance for your suggestions.