Of course things are more efficient now. But the real question is-- does that make our lives better? Is an efficient vacation a better vacation? What would an "efficient" vacation look like (the idea sound gross to me. Getting lost and overwhelmed are part of the fun for me).
Simply put, efficiency taken to a logical extreme is bad and we should acknowledge that.
Efficiency is about your optimization goals, a guy like him is optimizing for free time that is why he optimized the rest of it to such a degree, that he can afford it without changing the whole thing for the worse.
He could easily also have used that free time to do more work, but he refused.
I used to think that more free time was a key to happiness. Turns out I don't believe that at all now, and most of my free time I spend browsing internet garbage.
I realized that I enjoy challenges and being needed is actually very fulfilling to me, and not something I can just artificially make happen in my free time. As such, perhaps in a more efficient world (where I don't help my neighbor fix their car, don't cook with roommates) I am less happy.
This isn't to say efficiency isn't often good, but I think some of the things it may cost (e.g. fewer possible friendships) may not be worth the price.
And that's just vacation travel. The author casually mentions that Uber and Lyft supplanted "hailing cabs" as if it were not much of an innovation, when we all know what the experience was like if you were in any city less dense than New York...it was a pain in the ass to get a cab and it was usually way more expensive than it was worth and the cars were hardly ever clean and you had no idea what kind of driver you were getting. You were also lucky if they took a credit card.