I'm not so sure. There are literally thousands of hotel rooms on site that sell for less for $95-$150 per night. And thousands more selling for $185-$225. Indeed, on any given day, there are more on site rooms selling for $225 or less than all other rooms combined. It is hard to make the case that the size and scope of Pop and All-Stars and AoA and Caribbean Beach and POR, (to say nothing of the campground), reveal a strategy of focusing exclusively on the upscale customer. And Disney knows that over 50% of its daily guests are staying off site for less than $150 per night. Disney could have built a Four Seasons style hotel and a Waldorf quality hotel. It chose not to, and instead sold (leased?) land to those companies so that they could build upscale hotels.
I think that the proliferation of fenced off area events is simply Disney's nod to the fact that WDW attracts visitors of every income and interest level, and that the upper end of the income strata was being underserved. I don't say the following to insult anyone, and it is not me projecting my views, but it is reality in the travel industry, and that is: Disney figured out that there is a healthy slice of the population who can afford to stay in Deluxe resorts and will accept nothing less. And many of these same people do not like the fact that once they cross through the turnstile, they "join the masses" and get no better or no different experience than any other person who drove in from their Day's Inn earlier that morning. They want an upgraded experience that includes add-ons and exclusive access. And other than a few tours, up until a couple of years ago, Disney offered very few such opportunities. It is simply capturing that underserved market. And there is also a slice of the population that wants an upgraded experience with add-ons and exclusive access and is willing to pay for it, even if that means that they have to stay in less expensive resorts, or even off site, in order to afford those experiences. There are people who do not want to be "one in 50,000" once they enter the park. They want their experience to be unique, more exclusive, and (in their minds), "better". Disney was leaving a lot of money on the table not sucking money out of these people's pockets. In 1990, anyone who wanted a "great" viewing spot for the parade camped out for two hours to get it. Now, you pay a fee to get it. None of this is suggestive of a business strategy that "is only interested in an upscale customer." Rather, it is suggestive of a business strategy where Disney realized that there are vacationers who value "buying their way out of the crowd" and that it was failing to separate those people from their money. Not at all unlike the American Express Platinum events or experiences. I will admit to spending quite a few shekels on some of those. But not nearly as much as Amex would like! So far I have resisted doing that at WDW because I find that the "pedestrian experiences" that I am getting are sufficient. But I can't say that this will always remain the same.
