When I was growing up, we lived an hour away from WDW - all we ever did was day trips, and it was usually for my birthday. My parents and I would get up early in the morning and head out, always stopping for breakfast at McDonald's in Clermont. We would be at the MK for rope drop, and we would go go go all day long until the park closed... then make the trip back home.
The first time I ever stayed on-property was well into adulthood with my husband and our four children. We were there for a few days, but it was during Spring Break and miserably crowded! We weren't used to dealing with those kinds of crowds, and we vowed never to go during that time again. LOL We had to move out of state for DH's job for a few years, and we never traveled back home during the years we were gone just to vacation. Once we moved back, though, it was game on!
Since we've gotten APs, and although we live close enough (2 hours away) to make a day trip, we prefer to go down for a few days at a time. We really enjoy taking our time and not feeling like we HAVE TO do everything in one day! We've stayed on-site when we could get a really great deal on a room, but more and more, we are choosing to stay off-site in a suite hotel that is very close to Disney property. The novelty of staying on-property has worn off quite a bit, simply because our dollar stretches twice as far when staying off-site, and we'd rather spend the money on other things than a room that we're only going to sleep in. The other bonus is the off-site hotel gives us separate bedrooms and a full kitchen, so we save even more money by having some of our meals (good, home-cooked food) in our room. DH and I have plans to stay at all of the Deluxe hotels at some point in time, but those will be special trips when we feel like splurging.
Our last trip was over Labor Day weekend - we went kid-free with another couple, and we had a blast! We slept-in every morning. We ate a few overpriced meals in Signature restaurants. We went to DHS just to ride ToT and RnRC. One day, we didn't even go to a park - just went to Poly for an impromptu dinner at Kona Café. We relaxed in the pool and hot tub. It was so easygoing and not once did we feel like we had wasted the weekend! We did "plan" park days, but I use that term very loosely.
Oh, and we avoid the super-busy times - we don't go during Easter week, June/July/August, Thanksgiving, Christmas/winter break. However, we chose to get the regular FL Res AP instead of the SP, because we don't want to have any blockout dates in the event we DO want to go during those times. Next year, we might add on the water parks - not sure yet.
In a nutshell, we feel like we enjoy WDW far more as local-ish folk than we ever would if we could only go for a week or two at a time every couple of years. I feel like we can plan as much, or as little, as we want, without feeling like we're missing out on anything. Having the option to do something "next time" is fantastic, because we know "next time" is probably in a couple of weeks or so.
I'm distracted at the moment, and I feel like I'm rambling, so I'm going to stop here.
