I've upgraded annually and only lost $50-$70 on the 16gb version (selling after announcement but before launch). That made it very easy to keep upgrading for essentially no cost (or less than Apple Care). The last two times- 32gb iPad 4 & 32gb iPad Air, I've sold for way less. Not that I don't love my iPad Air 2, but the "cost savings" isn't quite there anymore like it was. Resale market is definitely worse than before.
11/25/14 at 12:08pm