If you're like me and you take your digital music collection seriously, then I highly suggest that you check out Mediamonkey. It allows you to manage a collection from 100 to 100,000+ digital audio files, audiobooks, Podcasts, playlists, etc. Organize and browse your collection by genre, artist, album, album art, rating, mood, etc, etc, etc. In addition, it's compatible with almost every portable MP3 player out there and it allows for direct synchronization and it even let's you transfer songs from your MP3 player back to your computer (even with an iPod). But that's not even the cool part! Mediamonkey is 100% totally skinnable as well as customizable with it's built in scripting feature and even if you're not hip-with-the-script, there are LOADS of pre-made and downloadable scripts available that will allow you to maintain and manage your collection by allowing custom views and features based specific user based criteria. For example, my personal favorite is a script that will allow you to directly search Discogs, Wikipedia, LastFM, Amazon, etc all within the program so you can have a properly tagged MP3 collection. It's really fucking amazing and EASY to use. The interface is very similar to that of (gag!) iTunes so if you're familiar with that, Mediamonkey should be a seamless transition, but even if you're not an iTunes user, Mediamonkey is wicked easy to operate thanks to it's non-complicated help file, built-in tool tips, and it's extensive online forum.
The absolute BEST part of Mediamonkey is that it's FREE and I don't mean free as in cracked, patched, or key generated, but as in you can go to the Mediamonkey website and download the basic program for FREE. There is in fact a Gold Version of MM that has quite a few more bells and whistles, and it would only set you back $19.95 (US dollars).
I hardly scratched the surface describing the features, if nothing else; stroll over to their website and peep the features yourself. Simply put, Mediamonkey is the mutt's nuts and if you take your music collection seriously, then I highly suggest that you download it immediately and re-take control over your music! Trust me on this one!!!