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If you don't mind paying for your software J.River Media Center is probably the single most powerful iTunes-like media player/organizer for Windows. They also have a free edition, but that only handles music (and not e.g. video).

The best I know of is either J River's Media Jukebox 12.x (freeware), or WinAmp 2.95/5.x.
J River's most recent app is shareware: J River's Media Center 14.x.

If you don't need iTMS, there are plenty of iTunes-like players out there that provide similar syncing capabilities for any hardware that mounts as an USB drive. For Windows, my personal recommendation is the free J.River Media Jukebox. On Linux, just use whatever is installed by default in your distro (Rhythmbox, JuK, Amarok) - they can all do that. If you still want a good lightweight Linux alternative, try Quod Libet.

Amarok's all right and all, but it has one serious failing - it doesn't seem able to do gapless playback. Given that Ogg Vorbis is the geek audio format of choice, and that its biggest USP (for me, anyway) is proper gapless playback, why hasn't it been implemented in Amarok from the beginning? Or am I just stupid and missing something, and it's somwhere that I haven't managed to find?

Also, it needs work on its playlist manager. The simple drag-and-drop interface is nice, but it shouldn't go by how you organise your music files on your hard disk. It should sort your music by the tags on the songs. That's what they're for.

Why isn't there a really competent all-in-one media player/ripper/organiser out there? There seems to be nothing that gets anywhere near something like Media Jukebox for functionality. SnackAmp is decent, but its user interface is messy (and it doesn't seem to know what FLAC is, nor in fact do many others). Rhythmbox and JuK are just rotten. It's a bit frustrating, really.

MJ has had the "make a playlist out of query parameters" feature for years, but takes it further: you can define custom fields in the database and search on them (though to be fair, iTunes already includes the things I used those custom fields for.) More importantly, its notion of (non-dynamic) playlists is much more flexible -- you can use a song's presence on a static playlist as a query parameter for a smartlist. I've come to think of playlists as a way of attaching attributes to songs. It's a much more flexible, nuanced way to represent things like genre, where multiple values can easily apply to a song.

How is that useful? Well, for example, I have a playlist of background music for dinner parties. If I'm serving Mexican food one night, I can whip up a quick smartlist that says, "Play all the songs on both the Dinner playlist and the Latin playlist." Or better, if I decide I only want instrumental pieces, "Play all the songs on both the Dinner playlist and the Latin playlist, except ones on the Has Lyrics playlist."

As far as I can tell, other than putting lists of keywords in the Comments field and doing string searches, there's no way to do flexible user-data-driven queries like that in iTunes. You can add a song to a playlist, but the playlist is a data sink -- you can't leverage it for anything else. (If I'm wrong about that, please clue me in!)

MJ also has a robust plugin interface for audio codecs, rip/burn capability, a built-in sound editor if you want to make a mix CD with fancy effects, ReplayGain support (same as iTunes' volume leveling), and supports downloading to a variety of portable MP3 players. The latest incarnation can also manage libraries of video files.

Other than the selection at the iTunes Store, I don't see a single thing iTunes gives me that I haven't already been enjoying for years with my existing software.

Media Jukebox has had dynamic query-based playlists (they call them "smartlists") for years. WinAmp has been blown out of the water by MJ for so long I doubt it's even damp any more.

No one's forcing you to use MusicMatch with the iPod, there are a number of superior solutions available, one being free.

- Ephpod
The free one, designed for transferring to the iPod and nothing more. A lot of people use it and love it, it has a simple interface, and allows you to download the weather and other fun things to your iPod.

- XPlay
Another product designed specifically for iPod management. It integrates with Windows Explorer and allows you to drag-and-drop your music into a special virtual folder on your iPod's hard drive in order to transfer music, a feature that a lot of people love. Optionally, you can choose to use Windows Media Player to synchronize by using a plug-in included by Mediafour, the developers.

- Media Center
My personal favorite solution, Media Center. It costs $40, but it's a fantastic media management program, featuring smart playlists, video playing, and a whole bunch of other features that are too many in number to attempt to mention here. Check out the 30-day trial that they have and see if you like it. It's also the fastest program on the Windows platform when it comes to synchronizing with the iPod.

By the by, Audible files could be transferred to a 1st or 2nd generation WinniePod by using Ephpod or Media Center, and now Audible has made a program available to transfer audiobooks as well.

A little off-topic, but check out media jukebox. I have tried out zinf and any other music player for Linux I could find and have yet to find another program that equals media jukebox in overall functionality but especially in terms of how it organizes your music (you can set up custom views of your music, such as by Genre / Artist / Album, etc...). It supports ripping and encoding to pretty much any format. It also has a great plugin system for transferring files to MP3 devices as well as having CD Burning functionality. If I had any coding skills I would love to bring something like this to Linux. I believe the next version will fully incorporate TV viewing, scheduled recording, etc... If there are any coders looking for a good program to emulate I highly suggest this one. (Std disclaimer; I don't work for j river, I just really dig their program)