Whether it be with Linux, OS X or whatever, in the end many people have found themselves in a position where access to select legacy applications are a must. Sadly, most people are under the impression that WINE is the answer to many of these problems. And while WINE can be helpful with some Windows apps, perhaps even majority share of them, there are still countless others in which this technology is not going to be any help at all.
This becomes painfully true with things such as syncing up your iPhone with iTunes. Not because of music, but just to get other levels of functionality out of it such as software updates, ringtones, etc. To make this happen, WINE is not going to help you. This is why I myself rely heavily on virtualization options such as VirtualBox.
With an old install of XP Home, VirtualBox allows me to do practically anything I might need with legacy applications. Even better, is that I can put it into seamless mode and then I have a much cleaner blending between the two operating systems. Ubuntu and Windows suddenly become less of an issue, while being able to simply use the application I need.
Why bother? Simple, I only have the need for legacy apps on occasion while preferring to run Ubuntu as my native OS. So this proves to be a good solution for me.