My view is that if you have NEVER been to DisneyWorld, some level of planning & basic knowledge is helpful since there are 4 parks and MANY hotels to choose from. Knowing, for example, that the Contemporary is considered part of the Magic Kingdom resort area is important when driving on the property or else the cryptic road signs can be VERY confusing for a first time visitor. Not sure how you can plan to eat at X on Wednesday, if you have no idea if that restaurant will appeal to your family. I don't find restaurant reviews helpful since they tend to involve so much personal preference. For the same restaurant you will find as many who say the service was 'too slow' as those who say it was 'too fast'. If you are a regular, then you probably already know what your family likes/doesn't about Disney.
If you are tied to a rigid schedule, you will probably not enjoy the experience as much. There are also the practical aspects of a ride being down for maintenance or lines being longer/shorter then you estimated. Going to work involves a certain level of structure and routine. Part of the reason we go on vacation is to do something less structured.
to the DIS! This is definitely the site for planners. Have fun!
