The prospect of getting an upgrade is pretty uncommon and not anything you have any control over. Getting multiple upgrades is going to be downright impossible. It is a bad way to start off your trip when you expect something that is pretty far fetched that you are going to get.
You say that you read lots of stories about upgrades. These types of threads come up weekly. About 10 - 14 people will respond that, yes, indeed they did receive an upgrade. But considering the fact that there are over 32,000 rooms at Disney that can be occupied in one week, that is a rarity; not lots of stories.....
Quite frankly, over the past few years, Disney has added booking categories based on requests at the values and moderates. And people are paying for it; waterview, riverview, preferred, etc. It makes the prospect of upgrades even less; people are willing to pay for it and if it is something you want, you should be prepared to pay for it too.