I think I see things differently as I live 15 miles away from Disney.
You would be utterly amazed at the number of locals who dont go anywhere near Disney property. Disney does things to lure them to the parks.
Annual passes are not a loyalty program. They are a way to bring people back again and again so that they will buy food, soda, trinkets etc.
Loyalty programs are not about saving money. They are about showing appreciation for your patronage and to entice you to keep comng back to spend more money..
In order to get a free cup of coffee....you need to buy 10 cups at full price.
In order to earn frequent flier miles...you need to fly frequently.
I dont save money buying 10 cups of coffee....but the loyalty card entices me to go back to there as opposed to going to Dunkin Donuts.
I might find a better fare or schedule at another airline, but I'm loyal to the same airline because I earn the miles and might get a "free" trip somewhere. No money saving there either.
I'm pretty sure I dont know any other way to explain this, so I'm done.
I'm very happy that some people are pleased with this program and see a value. I dont.
Not to belabor or argue...but I don't see a lot of difference. The problem is you are comparing completely different businesses in some examples like the airline.
But the comparison on some coffee shop free coffee after purchasing 10 vs. the seasonal annual pass - they are similar. It's whether you pay up front or over time. And it assumes you would have bought the coffee or gone to the park anyways.
In the case of the coffee, say you have to buy 10 cups of coffee, and then you get a free one. You still have to come in repeated and buy those 10 cups at normal price. You don't HAVE to buy anything else like a donut, a breakfast sandwich, or anything like that. But you do, because you are there and it is convenient. So they make money by making you come back repeatedly for the cost of a cup of coffee.
The pass situation is a little different in that you have to pay up front. You pay a larger amount, but then you get to go to the parks for free for a period of time. You still don't have to buy anything else. But you do, because you are there and it is convenient. But you get your savings by getting to come back more frequently, and Disney still makes its money.
It's basically the same as if the coffee shop said you could pay for 10 coffees up front, but you would get 11 coffees, as long as you didn't get them all at once.
Pay up front, pay over time - end result is the same. You saved money, they made money. They made slightly less.
But if the incentive causes you to go MORE than you would have - you probably wouldn't have kept stopping for coffee every day, or you wouldn't bother going to the park, THAT's when the company gets revenue - on the ancillary sales (the donut) they otherwise wouldn't have, but the consumer at perceives they got value - although they probably spent a lot more than they would have. Because the value perceived was not necessarily monetary.
I still agree that D23's cost in relation to the thusfar announced benefits isn't great, but like I said before I'm placing a bet that the benefits that they HAVEN'T announced yet (and they very specifically said they haven't announced them all yet) will help change the perceived value. How about 10% off everything! I'd at least like to see some discounts on MYW tickets...the DVC discount on the AP is nice, but it won't always make sense for us.
Certainly Disney could do more in the way of "loss leaders" to reward us for our loyalty - but from a business standpoint, they'd rather throw the loss leaders at new potential repeat customers than those who are already spending money with the company.
And apparently now fudge also to top it off! 
