I must say that when we went in 99/00 having never been, we were clueless. The trip was my MIL's idea, she booked the hotels back in like 1993 or 94, she paid for the hotels for all of us so no thought was ever given by us as to where we were going. She booked a couple of dinners and one character breakfast for our group. We saved our money, packed our bags, rented a car and jumped on a plane for Florida. We were DL veterans so it didn't occur to us to think about planning.(DL is much easier to navigate given it's smaller stature) We showed up totally innocent, unaware and naive. We had a really good time but could have done so much more. ie on New Years Eve our son was having anxiety attacks(didn't recognize them at the time, now we know) the Y2K thing was huge, WDW put flashlights in our hotel rooms on the 31st (just in case) and there were "hidden" generator type lights all over the place (just in case). Needless to say, we opted to stay out of the parks on New Years Eve since everytime we tried to get on a bus to go our son puked! Had we know all of the options we would have spent the day doing other things, touring hotels, boating, camp fire at FW etc..... We spent the day swimming, which was okay, but...... We didn't know any of this stuff existed. I am pretty organized and can't really say why it didn't occur to me to be more informed, but we weren't. The ease of the internet has made trip planning so much easier.
I am sure there are lots of folks out there who are just like I was the first time around. Each to their own, some people plan some do not, some are organized some are not, that is what makes us all different. Planners have lousy vacations also and non-planners like me above can still have a great time despite total ignorance.
With this trip, my first decision was finding a hotel and it sno-balled from there. I was researching hotels, then I found this board and a few others and have been obsessed ever since. We are not planned out to the minute, we only have a few ADR's for the places we wanted, a couple of dinner packages, (we opted to not do the dining plan, but feel we made an educated decision based on our family dynamics) and we know a ton. We have a plan of attack for the parks and New Years Eve, there are some must do's and some if we have time, energy or inclination. We are excited and can hardly wait to leave.
Please enlighten me!
I found it very hard to keep a straight face when I told her that the Disney Tranportation system will bus you to all of the parks in WDW. She looked me in astonishment and said she didn't know they had buses. They spent the extra money to stay at the Contemporary so they wouldn't have to rent a car. 
Let the fun begin!
)
