My first trip was in 1996 with then GF, now DW. We stayed a few nights off site and went to US and SW for one day each, then stayed at Clearwater Beach for a couple nights, then stayed at CBR for three more nights and spent a day each at Epcot and MK. I had never even been to Florida, let alone Disney World. Dad was never interested in taking us. He liked nature/history trips and avoided large cities and crowded areas like they were leper colonies. DW had been before, so she remembered some things, but not much. We really were winging it.
We were there during Labor Day week, so the crowds were low. We spent some time at the Boardwalk. I remember being able to see the Eiffel Tower replica in France at night -- that stuck with me. I also remember seeing the YC/BC across Crescent Lake and thinking, "that must be where the rich people stay." I really don't remember where we ate other than the ESPN Club. The only thing I remember being annoyed by was the nearly complete "cake castle" transformation -- still shake my head when I think about it.
Five years later we took our three nephews, then went the year after with another couple (no kids on that trip), and are now planning our third trip with our own kids for next May.
OP -- I want to thank you for starting this thread, because it helps to bring back some of the magic and keep things in perspective while planning another trip. Our last trip felt a little bit forced, and I want to loosen up more on the next one, which I'm sure will be fine with the rest of my family. So... Thanks!