I have some sympathy for the booking view in an individual context -- but I think the issue is that it seems like the sole reason for a lot of surprise winners is solely to BE a "surprise" on a given night, and not as a part of the plan.
I don't think anyone really has a huge problem with Charlotte winning, for instance, other than they really think Sasha Banks is amazing and that "Ric Flair interfering every damn time" is the exact opposite way of making a longer title reign feel important.
A lot of people had a problem with Zack Ryder winning (I didn't; those matches are exactly the ones where "fluky" results make the best sense) because having Zack Ryder listed in the listed of IC champions diminishes the title (if that's even possible any more) and because there was clearly zero plan for Zack Ryder to ever be anything at all.
The larger problem is that there is zero hierarchy or grand plan whatsoever, and Ryder personifies that. He beat Jericho (who of course just beat AJ Styles, who is your #1 Contender, all of which happened in the last 10 days) on March 28; before that his last WWE Raw singles win was
.
And of course then he loses via the distraction-finisher (guaranteed 5000% more effective than the actual finisher, while building the winner 5000% less effectively) to The Miz, who if you wanted him to have the Intercontinental Title just give it to him in the ladder match ffs.
So why should we care, if the people running the show don't?