Apple removed the DRM from new music sales. All existing music sold before then is still DRM locked. When Apple discontinued DRM, they made user spend $0.30 per song to unlock them (seriously). Now, it appears you can spend $25 for iTunes Match, ensure the affected songs are available, delete the local DRM-infected ones, and it will download proper ones to replace them.

iTunes Match brings its own issues to the party. I've had songs that I own, with 'explicit content', that I've hand-ripped, converted into radio friendly abominations that are, frankly, unlistenable. Maybe that's just Apple's 'family-friendly' values shining through; that might be appropriate for some, but I don't have a Big Brother in real life, and I don't want one messing with my music collection either!

You can redownload DRM-free versions for free:

http://www.wired.com/2014/03/kill-itunes-drm/

There were programs for removing the DRM from iTunes files. I used one successfully. Maybe they don't work anymore? I don't know.

Or you can burn your DRM songs to CD, then rip to DRM-free MP3.

Encoding music that has lossy compression with a lossy compressor? Not a good idea ;).

Know a good music player for Windows? And don't tell me Windows Media Player. :)

http://www.foobar2000.org/ is a fantastic piece of software. Extremely efficient/powerful/customizable (and closed-source). I sorely miss it under Linux, Rhythmbox/Quodlibet/Amarok/Clementine don't even come close.

What powerful features does one need in music player? Or, what features do you miss in OSS players?

WMP actually isn't that bad these days, though all I use it for is ripping CDs (yep, those shiny plastic things for you young'uns) since it's great at that. For playback in Windows, I've stuck with Winamp through the years as I haven't found anything that works the way it does without a bunch of features I don't need. I tried Foobar2000 and couldn't get into it, and MediaMonkey just seemed like overkill.

By the way, a great site for finding apps in specific genres is alternativeto.net. Here's a list of alternatives to iTunes:

http://alternativeto.net/software/itunes/?platform=windows

I'll never understand this community...downvoted because I use WMP (oh the horror), or downvoted because I was trying to be helpful?

I moved to Linux (Ubuntu) and migrated a HUGE iTunes library along with it. I now use Clementine as my music management / player. I believe there's a way to import an iTunes library, but the iTunes metadata is all in one big XML file. So I wrote a script that loads all my metadata into Clementine's sqlite database.

I can't tell you in words how awesome this is.

http://www.jriver.com/

But I have used it for 10 years and it's the only reason I still have Windows machines in my house. It's that good.

Winamp is still my preference.