After seeing how mine look in the (hopefully very beta) iOS 7, I'm ready to sell half of mine rather than deal with UI updates.

Money where his mouth is? Although it would seem unlikely unless he had a prior glimpse of what was coming. Is this that unlikely?

Although he wasn't aware of the exact details or extent of the changes, rumors of a total overhaul have been circulating for months. He probably anticipated having to input hundreds if not thousands of hours of development time to prepare for iOS 7. At the very least, this must have been a factor in his decisions.