Even Being from Chicago, we go to WDW about 1-4 times a year (Average over the past 10 years comes out to be about 3.2
visits per year... yup coming up on trip 32!!!!). We have stayed in the Deluxe, Moderate, and Value resorts on property, and have also hit the "low end"..... <YUK>.... and "moderates" off property..... As many posters have chimed in, its in what you plan. When we go alone, we usually stay just off property in a Hampton Inn, or a Radisson, (etc. etc.) or if a really good deal is going.... at one of the locations near Downtown Disney.... When taking the Gang ( Sisters Family's, Inlaws, Parents) we usually do the "moderates"... the Delux has been for usually for special ocassions.... When touring with groups, no matter what Disney Resort your staying at, its about options.... like someone getting tired and taking the disney transportation system back to their room, or park hopping with a meet-up.... Staying on Site is PERFECT for impressing the folks, or for coordinating groups with different tastes.....
BTW: Going down to WDW next week, and got the Hampton Inn Maingate East for about $44.00 a Night... Virtually identical to an "All Star", and almost as close..... Needless to say, this is going to be a "power park trip", no friends or relatives.
Just food for thought.... I also have my preferences on the Disney properties based upon their transit options, and how their bus stops run...