Mark,
There are quite a few options available in the Windows environment which have a significant following: Media Monkey, Winamp, J River, and Foobar2000 being perhaps the most prominent. I'm not sure you'd get a very strong consensus for one of those over another, but I'd say that the people who have been into this computer audio thing for a long time, and have tried everything, like our Vincent Kars and Chris Connacker of Computer Audiophile - and I'd put myself in that category, too - tend to gravitate toward J River. Here's a roughly prioritized list of things I look for in music library manager and playback software:
1. Good support for bit perfect output. This means two things to me: automatic detection and output of native sample rate and bit depth, and ability to bypass the system audio mixer through support of WASAPI, ASIO, and/or WaveOut protocols.
2. The ability to define and easily edit a broad range of tags. The larger and more eclectic your music collection is, the more important it becomes to consistently categorize it in the ways to want to browse and search it. This means being able to define the categories (tags) you want, and easily edit them.
3. Related to point 2, be able to easily define and select various "views" of those tags to use in browsing your music collection. Can you define simple, cover-based views for just scanning your collection, or easily switch to very specific views designed to browse, say, chamber music? When your collection gets to 1000s of CDs, this gets very important.
4. Good performance with large libraries. Most libraries now have good performance with 50,000 to 100,000 tracks - but not all.
5. Good remote control support.
6. Support for a broad range of audio formats. For an audiophile, the "must have" format support is, IMO, FLAC, WAV, AIFF, MP3, Apple Lossless, and AAC. WMA lossless and WMA are nice to have. You can always use various converter programs to convert into the formats your player supports, but it is inconvenient. Given the broad availability of free library code to support these formats, lack of support indicates either laziness or deliberate attempt at locking customers to a format for business reasons.
7. Good internet integration. This means support for various internet radio stations, and ability to retrieve information related to the artist, album, etc you are playing from such diverse sources as WikiPedia, Amazon, Last.FM, AMG, etc.
8. Support for high quality DSP manipulations, such as oversampling, equalization, and convolution (used in room correction, for one). At minimum, it is nice to have the player directly support "VST" plugins, of which there are many available in all of the above categories. Foobar2000 is probably the king of this category.
9. Some history that suggests this is a long-term, sustainable company that won't suddenly leave you without support or enhancement.
J River scores well against all of those criteria, and stands above in 2) and 3). Foobar2000 is the Swiss Army knife of DSP audio manipulation, but the interface is less than stellar for me. WinAmp and Media Monkey have their adherents; I'm not fond of the MM interface personally, and WinAmp offers little for me that J River doesn't do as well or better.
You'll notice that sound quality has no place in my list. See this thread for why:
http://www.whatsbestforum.com/showthread.php?2703-Do-media-players-have-a-sound
I've found that, under truly rigorous comparison (listening to the same track dozens of times over, through different players, focusing on different subtle details each time), different bit-perfect players sound identical to me, even on very high resolution stereo and headphone systems. And any differences between them must originate in the first order with hardware, and switching to new hardware requires far less investment of time and learning than switching players, once you've really gotten to the point of fully utilizing a particular player.
As an aside, iTunes scores mediocre to poor against all of my criteria. This is a primary reason I use PC instead of Mac for music server hardware - in a music server, your media software pretty much IS your operating system. And there just aren't substantially better alternatives to iTunes on OSx at present, although the open source Songbird has some significant advantages.