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My gen1 hasn't missed a beat with anything I've thrown at it in the last year, so I haven't felt the need for 'more'. But I did make sure to get one of the heavier-hitting ones. Work has been large, image-heavy indesign docs, mid-weight illustrator work and batching stuff in PS. I can't see it failing me in the next 12 months either really. Conversely, the Apple wisdom of always buying the best you can probably applies.
iPad pro doesn't run InDesign tho. Manages surfing the web semi-pro just fine. I would say 'portable' instead of wee, but once you're used to it everything else does seem a bit monster big. Screen bezel is smaller than on the air so you do get a bit more screen for your inches, but still smaller than the 13".
as I've said on this thread many times, I love mine (1st gen, 8gb ram, 1.4ghz). Gone from hating the days when I have to lug my 15" in to town to carrying this one around every time just in case.