In reply to iksander:
Having been a MediaMonkey user for some time now for my music library, I finally installed iTunes to connect the my iPad. And, by comparison with MediaMonkey, iTunes sucks.
Basically, the difference is that, like all Apple products, Apple/iTunes is in control, the user is not. You work the way iTunes tells you, or do what it allows you to do.
The other thing to remember is that Apple is primarily a media vendor, and the devices you buy are portals to their shop, which they very graciously allow you to pay lots of money to buy; it's a bit like having to buy a checkout to shop in Tescos... So iTunes is geared up for you buying music from iTunes, and not so keen to help you use media you've obtained elsewhere; it will do it, but somewhat reluctantly.
With MediaMonkey, the user is in control; it will do what you tell it, including fetching music back from an iThing, whilst undoing the filename obfuscation that iTunes applies when transferring music to the device.
MM4 will allow you to create multiple sync lists from your music library, and will recognise and sync your devices individually, with level of automation that you choose; you plug the iThing into the PC with MM running, and it will appear in the browser, and auto-sync, or not. These devices can be iThings, USB-interface music players, disk drives, etc.
MM will transfer cover artwork (in the album folder) to the iThing, and it will be visible on the iThing. iTunes did not.
MM can be installed as a 'portable' installation, which means it will run from whatever disk it's installed on; this means you can have your media library and MM on a portable disk, and take it with you, provided you have a Windows computer to plug it into to run on; MM is Windows-only.
MM will integrate with Amazon's Downloader, and even with iTunes, if you purchase music online. You can tell it to scan the download folder every time you start MM, or do it manually. You can tell MM where to find music, and it will listen to what you tell it, unlike iTunes, which 'helpfully' ignores your instructions, and goes off and puts everything it can find into your library, from places you haven't asked. So, if you have uncompressed and compressed libraries, it will include both. If you then delete the unwanted music from the library, it will actually delete the music from your computer (fortunately, I spotted what it was doing before my waste basket filled up); MM gives you up to four choices of 'remove'.
MM4 also handles video, but I have no experience of it. Oh, and it will handle FLAC for good audio quality; on an iThing, you'd have to go proprietary ALAC. MM comes with the LAME MP3 encoder, but with a 30-day limit: easy to get around; simply download and install a new version of LAME over the top, and it will never complain again.
MM is free, or you can pay a one-time fee for a 'Gold' version, which includes some extra features, like adding genre filters on the Auto-DJ. I've managed without paying so far, but, given how well it works for me, I may just pay up out of gratitude...
I'm sorting out a mate's music library at the moment, which has moved from WMP to iTunes (and now to MM). And it's a mess, with lots of copies of music created by iTunes, often to get around the fact that iThings won't play WMA or other formats. As an example of the idiotic inefficiency, I found its cover artwork library, also obfuscated like the music, and with a proprietary 'tweak' to JPEGs so they're not visible as pictures on the PC. Having removed this tweak, I discovered that, of the 3000+ pieces of artwork, there were about 330 unique pieces of artwork; all the rest were identical duplicates.
I still have iTunes installed (reluctantly), to provide the device driver for the iPad, which MM relies on to communicate. It's a bit galling to have to install nearly 0.5GB of crap software just to provide a device driver; iTunes is also bloatware.
Phew; that was a bit of a rant, and I'm sure other people will point out lots of errors and misunderstandings on my part. But it's not just me...
https://www.google.com/search?q=i+hate+itunes