The upgrade process in each case was painless. To set up the MBP, I just connected it to my Time Machine drive and was up and running about an hour later with all my apps and preferences intact. The iPhone took even less time than that and everything from my old phone was magically there. Snow Leopard took 45 minutes and, aside from a couple of Mail.app and Safari plug-ins I use, everything was just as before.1 Past upgrades of Apple computers and iPods have gone similarly well.
Which is where the potential difficulty for Apple comes in. From a superficial perspective, my old MBP and new MBP felt exactly the same…same OS, same desktop wallpaper, same Dock, all my same files in their same folders, etc. Same deal with the iPhone except moreso…the iPhone is almost entirely software and that was nearly identical. And re: Snow Leopard, I haven’t noticed any changes at all aside from the aforementioned absent plug-ins.
So, just having paid thousands of dollars for new hardware and software, I have what feels like my same old stuff.
I’ve experienced the same, seamless transition: going from my old iBook G3 to my new sexy MacBook Pro, and going from my first-generation iPhone to my iPhone 3GS, and upgrading the OS from Jaguar to Panther to Leopard – once I ran the update process, my wallpaper, applications, settings, and files were all right where I had left them. But I’ve always considered that a feature, a plus, not a negative, because in each case, I could see my stuff running faster and with fewer glitches or errors.
Taking away the jarring transition from one piece of kit to another, and dropping all the files and customizations I had been collecting and making for years prior, forced me to pay attention to the one thing (or several things) that had really changed: the underlying hardware was faster, or the operating system itself was more efficient and powerful.