While I upgrade my iPhone every year, my iPad upgrade history trends toward every other generation: iPad 2, fourth-gen, Air, and 9.7-inch Pro. Skipping a generation (with the exception of the fourth-gen to original Air) has served me well as each upgrade is less incremental and more dramatic.
(I later acquired the original iPad — seen above stacked on the new iPad Pro — to collect; the new 11-inch iPad Pro feels like the modern version of that design with similar flat sides and the bulbous back squashed.)
This time around I’m upgrading from the 9.7-inch iPad Pro from early 2016 to the brand new 11-inch iPad Pro. The combination of upgraded specs, an all-new design, and subtly improved accessories is making this step all the more rewarding.