You've hit the nail on the head, and I find it applies so many more things in life than just travel. It is my general observation that many people, as they progress through their life, reach the stage where they have more disposable income than time. And suddenly, all that tech fascination with self-service becomes extremely annoying.
I have personal examples from "the other side" for the cases you give.
Insurance-wise, I've been procrastinating on getting some of the belongings we have at home insured, because the insurance agent keeps coming back to me with calculations and offers I need to look at. But I have neither time nor patience to deal with it - especially not to study PDFs with tables full of calculations that were explicitly designed to be hard to compare[0]. The only interaction I wanted to have is, "this is where we live, this is the stuff we want insured, tell me how much to pay and where to send the money". They're losing money because they try to give me opportunity to save money[1].
Travel-wise, my wife and I both always looked down on people going on all-inclusives - but we took a chance and went on our first-ever all-inclusive a few years ago. We were immediately sold on the concept. It wasn't even a good all-inclusive - it was the cheapest one we could find, and the resort smelled like goats half the time - but it was the first time we actually rested. The amount of bullshit that goes into vacations is hard to even imagine until you experience being free of it. Even having to make a decision when, where and what to eat on a given day is a hidden source of background anxiety. On an all-inclusive, the only thing you need to worry about is what to do with all the worry-free leisure time you have.
So yeah, I agree with your conclusions. And in particular:
> people who are into custom stuff they want to do themselves (and don't pay) niche or get "all inclusive" and don't care about anything whales
Sometimes, perhaps often, those might be the same people. Personally, my all-inclusive experience convinced me that I should mentally separate the type of travel I want into categories. If I want to explore something niche, I'll continue to plan it myself. If I want to actually rest, I'll reach for the most bullshit-free all-inclusive experience I can get - as close as possible to "wire some money and be told what plane to catch".
(Though calling all-inclusive travelers "whales" is perhaps exaggerated - all-inclusives are ridiculously cheap these days, if you're willing to make compromises on luxury looks and you book far ahead in advance.)
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[0] - Because, of course, businesses are douchy like that.
[1] - Or, perhaps, to fail at saving money - because, again, businesses are douchy like that.