Transferring my Winamp library into iTunes?

Have you tried MediaMonkey ? I've been using it for several years now and would not go back to iTunes (or an iPod). It has an iPod sync plug-in, and a quick google search found that it claims to be able to import Winamp metadata, which I have never personally tried. There is a freeware version and a paid version that does more.

Does it have to be iTunes? Mediamonkey will sync with ipods, and also appears to import all that data from Winamp. Keeping in mind that I never imported similar data myself. But Mediamonkey has pretty active forums, I'm sure someone there could help you.

Itunes is the worst thing to ever have been sent to this earth. If the 2012 apocalypse is real, it will be itunes. I'm pretty sure itunes is Kyser Soze. OK, not really, but itunes starts to get really slow and clunky when you have a large music library, and you have a VERY large library. I would suggest you avoid it like the plague. I have used Media Monkey in the past and found it to be a very good program. It has been a number of years, so I can't say whether or not it is still good, but anything is better than itunes.

If you wanted to do itunes, you could always try it and see what happens. Load it up, open it, and have it scan your songs. I would suggest you back up your music, though, since you have so much attachment to your ratings (and it's a good idea to have a library of that size backed up anyways). I don't know if itunes would damage anything on import, but a backup would keep this from being a catastrophe. Also, itunes has a feature where it automatically organizes your music into artist and album folders. This is great if you have itunes import all of your music, but if you are importing music from somewhere else, it will cause itunes to make copies of every song in the itunes music folder, which is definitely not what you want.

iTunes really is the most terrible possible option. I've used iTunes, Media Monkey, Winamp, and Foobar2000, and I think Media Monkey is probably the best option for you. I did not import anything when I started using Media Monkey, but apparently when you first install and set it up, it gives you an option to import your Winamp database. So you can always install it and give it a try, and if it doesn't work the people on the http://www.mediamonkey.com/forum/ are pretty helpful.

I just about caved in and abandoned Winamp not too long ago, mainly because it would occasionally have an aneurism, its database would get corrupted, and I'd lose my podcast subscriptions, playcounts & ratings info. I think this may have happened once or twice when I accidentally opened multiple instances simultaneously. I too use ml_ipod to sync my iPod. Of particular importance to me was having a smart playlists feature, and quite simply, no other media player is as versatile in this regard as Winamp. In the end, that's one of the two things that prevented me from switching. The other was the Winamp Backup Tool, which lets me recover from a glitch quickly and easily. http://www.winamp.com/plugin/winamp-backup-tool-v1-0/222583

Not iTunes! Don't even put it on your computer.

I too have a large library, iTunes is not the app you want. Seriously, it will choke dead ducks with a library that size. I use media monkey for my music on the pc, and it is reliable.

Thanks, everyone. I'm investigating MediaMonkey, and I'll report back here...