I have seriously considered using various Disney packages before but I always chicken out. I can see though how someone could waste a ton of money, break even or perhaps even come out ahead (especially on Discovery Magic) depending on how well they took advantage of their package. I think that of all of the Disney packages the Discovery Magic offers the most flexibility and opportunity to come out ahead financially. But you would need to be very careful in deciding on what to use your wishes for in order for you to come out ahead. I think it would be a lot less stressful for you to plan everything out yourself and skip the package plans.
The deciding factor for me regarding packages is always thinking about all of the self imposed pressure I would feel to get my money's worth. I don't think I could enjoy simply sitting on a bench in the Magic Kingdom just watching people walk by because I would be thinking "Oh no I must get up - I have rent a bike, a water mouse and a pontoon boat - I have to eat at the California Grill, Flying Fish, Chefs De France, Artists Point, ect - I have to take the Undiscovered Future World, Keys to the Kingdom, and the Hidden Treasures of World Showcase tours - I must play a round of golf (both regular and minature) - I must get my money's worth on this darn package "- you get my point
I simply can't imagine eating enough food to ever get my money's worth on the Grand Plan or Deluxe Magic plans or by using the wishes for meals on the Discovery Magic Plan. My boyfriend and me will usually share an appetizer or salad (if we even get one), each have our own entree and share a dessert (again if we even have one). It isn't the cost that is keeping us from ordering all of the food - it is that we simply don't want it. I think a package would make us feel like we should order a ton of food we didn't even want in the first place. Then I would feel guilty about wasting food

Gee - I have way to much guilt about wasting stuff
Plus we sometimes like to eat at counter service restaurants and would feel like we were wasting money if we ate at one while on a meals included plan and wouldn't enjoy it.
In addition, all of the tours and recreational activities - golf, boat rentals, ect - sound nice but I know that by the 3rd or 4th day at WDW we start to get really lazy. We start to take lots of naps and start skipping sit down meals. I know there is no way we would ever use enough recreation activites to break even. Plus for the backstage tours there are usually nice AP and Disney Club discounts that make them much less of a benefit with the packages.
Plus I always worry about what I one of us (or both of us )gets sick and we spend our vacation in the room being miserable. This has actually happened once so I am totally paranoid about it happening again. All of that money you spent on the package is just being wasted. While if you didn't have a package you wouldn't be out anything more than your room and the food you actually eat.
We always have a general plan of what we want to do on our trip and have a general budget in mind of what it will cost. But we never don't do something we really want to do once we get to Walt Disney World. We like to sometimes be spontaneous and that is what credit cards are for
