It's hard. Also, there wouldn't have been Steve Jobs without that crazy and convoluted history. Getting fired from the company, then founding a new one then getting brought back?
People focus too much on the 'nasty' side of jobs, but it's easy to be nasty, and a lot of people do that, what's hard is having the other aspects that might be more subtle
in his biography (or most likely I read it somewhere else), the group that worked with him had a whole way of presenting things to him, that "made" him go for the best solution. It was a ruse, which he might have been aware or not, but it worked. And of course people were on their feet to present the best products
Jobs had a very finicky way of thinking about products, but I guess that created a dynamic in which other people that worked with him also stood for things that they believed in and that resulted in a balance of qualities that is lacking
Also Apple is not thinking about experience. When they took the floppy disks from the Macs I assume people were more than happy to see they go. Heck even display port has some advantages (you need one tiny interface to plug whatever kind of monitor you want).
Now we get a crapfest of different very similar cables with USB-C with different ports that look the same (charging/display/etc) and we killed an existing interface that for the most part works
And guess what Apple, your Keyboard and Mouse may be wireless and bluetooth but they still need an USB cable to be charged! Which cable comes with it? USB-A
I'm assume Steve would be testing the aerodynamic properties of the latest MB line, if you know what I mean