This is where dropbox has changed the game for me. If I can get at my stuff from anywhere, I don't care if it's the same device accessing it. Sure, there's some overhead to configuring multiple devices, installing software, etc. But this overhead comes with the advantage that if they are two different platforms, they have different strengths.

I have a desktop and a tablet. Needing to stay flexible between platforms means that switching the OS on either one is not nearly as painful as it used to be.