[lkmiller]

Of course, you need to be logged in to sync books from your account wirelessly. If you aren't logged in, does that Kindle still show as an option for "download & transfer"? And if so, do those books work on that un-logged-in Kindle if they have drm?

In other words, "download & transfer" might not do you any good on an unlogged-in Kindle no matter its age unless the book is drm-free (or drm removed).