To piggy back on the comments about machine learning, Netflix and YouTube still can’t get recommendations for suggested videos right, so I definitely don’t expect Disney to optimize things for my preferences. I would say it would be harder to capture accurate data on actual preferences since Disney didn’t collect data on preferences (e.g. whether or not someone liked a certain ride or attraction), and from the videos on genie, i don’t think selecting genres or kinds of activities is enough to provide me with an accurate optimized itinerary. I like IASW for sentimental reasons but won’t choose any categories that fit its description because I don’t care for other similar rides.
I will say though that they probably have optimized their algorithms as much as possible based on how much people have spent and where they have spent because it’s in their interest and because it’s a more accurate indicator of preference. For example, magic bands and reservations data have been collected on where people have chosen to eat, what they’ve ordered, what experiences they bought. I can see their algorithms making recommendations towards spending more.