I've got a problem; I've been a strong and relatively happy user of iTunes since it came out, since I'm also a strong and relatively happy user of MacOSX. Things have changed, though, especially since I no longer use an iPhone (for reasons stated in earlier posts) and my current phone, a "Google Phone" (Nexus One), running a 3rd party ROM, can play the free music file types OGG and FLAC. I no longer want to use proprietary music formats, such as Apple's lossless format ALAC or even MP3, so I need a method of music synchronization that can handle OGG and FLAC.
Now, I've been successfully using Salling Media Sync up to this point, as it seamlessly integrates Android phones and both iTunes and iPhoto. If you just want iTunes sync then I highly recommend it. It even handles OGG, since you can use plugins to get OGG to work in iTunes.
But for my current needs, I've tried:
Banshee is quite a long way from usefulness on MacOSX; it's a Linux project being ported. Songbird is just not quite there yet; you have to edit raw XML to get it to handle FLAC for my phone at this point, and I just couldn't get it to work properly. And even without FLAC, it failed on an awful lot of files, even with the lastest MacOSX beta version.
Doubletwist seems to work. Basically an iTunes clone, it handles OGG on my phone natively and handles FLAC by converting it to OGG on the fly, which is not the perfect solution but it's certainly better than nothing. I've been told that it will soon have a feature to defeat all media conversion and just copy the files, which would be perfect for me. In the meantime, it's a little buggy and slow, but it's free and it works.