Reading his laundry-list of paper cuts, it looks like many of them (around 50%?) relate to one particular issue: synchronisation. It keeps coming up, time and again, from his email woes (seriously, folks, didn't we solve this one back in 1980?) through to the borked address books, contact lists, and photo streams. Sync software usually takes a conservative approach to deleting or merging records, and leaves duplicate…
I have a business contact on my iPhone that has a contact photo of one of my relatives. I certainly didn't set it this way, but I have no idea how this happened. Is it something that my iPhone did? Is it something that happened at Google (it's a Google contact)? Is it something that my Windows 8 contacts app did (syncs to Google contacts)? I don't know, and even if I did, I don't know if I'd be able to fix it.
Frustrating. We sandbox our applications, and the success of the iPhone shows that this is something users want. Why can't we sandbox the other parts of our computers? Sure, I could "delink" everything and maintain it all myself, but I wish it wasn't so "all or nothing".