Just read some of the back and forth and why/why not Disney should do something extra for repeat guests. As someone who used to work in the hospitality industry with a degree in hotel management, its all about customer loyalty. This is why casinos and other hotels do it. They reward you for coming back for more, which makes them money. If you are a first time guest and you become aware of the perks returning customers receive, it makes said first time guests want to come back for more. Its all about enticing the repeat customer so although it may seem first time guests are "missing out" on these extras, it lures them back by seeing what they can get if they are loyal.
Though Disney doesn't have much competition in the theme park realm (nothing really on the same echelon as a Disney vacation), they DO have a A LOT of competition in tourism in general. Disney is always in competition with other luxury-style vacations like destinations (think Hawaii, Alaska), cruise lines, all inclusives, etc. Why do you think Disney got into the cruising and Disney
Adventures business lines? To have a leg up on these tourism segments. When a family plans their vacation for the year, Disney wants the loyal customer to return to their parks, or their cruise line, or their guided tour. They want people to think "disney vacation" again, rather than going to Sandals or taking an Alaskan cruise.
All that being said, it's been noted that Disney doesn't have much of a loyalty program (if at all). They don't need it. They entice people to come back by being unique and providing good service. The nostalgia factor is also huge. So unless and until Disney loses the repeat customer, I doubt we'll see any kind of loyalty program. And to monitor this, that is why they ask you how many times you have been.