As much as I hate almost everything, I always ask myself what's the baseline for those assumptions? How easy should it be to do the mentioned tasks?
Back in the days, we needed a camera and film, took pictures and get them developed, got a envelope and a stamp and finally sent the pictures to Mom. Obviously this is way more work than using the web, even if it's shitty.
I think we assume we could do things better and are used to things that work better without realizing the differences in their details which causes some tasks to be much more laborious than others.
There's this, and then there's purposeful degradation. A lot of the problem TFA describes were already solved properly years ago. There was a much better experience getting photos from your phone in pre-smartphone era, where you could just hook it up to your computer via the USB-to-some-propertiary-port cable and it would register as mass storage device. Web used to be much cleaner and better to use than it is now.
There is little thought given to quality and usability. We're churning out features and half-cooked solutions and moving on to the next fun thing. It might be OK in the past but today we depend much more on these systems and there is no way back.
Back in the days, we needed a camera and film, took pictures and get them developed, got a envelope and a stamp and finally sent the pictures to Mom. Obviously this is way more work than using the web, even if it's shitty.
I think we assume we could do things better and are used to things that work better without realizing the differences in their details which causes some tasks to be much more laborious than others.