WDW is much bigger than DLR and I've found that it requires a lot more planning and research. It's harder to be spontaneous at WDW (it's possible, but it always seems harder and more iffy to me). Some important questions: how many days will you be at WDW? What kinds of attractions do you and your family like? Are you interested in shows?
In general, WDW and DLR have very few attractions that are carbon copies in both resorts, but there are a number that bear the same name. Some versions are better at DLR, some better at WDW, and some are equally good. In general, I think WDW has better queues (also, more are indoors because the weather in FL is wet a lot more of the time). Some of my family's favorite attractions include: the Haunted Mansion, Seven Dwarfs Mine Train, Space Mountain, Tomorrowland Transit Authority (Peoplemover), Mickey's PhilharMagic, Journey into Imagination with Figment (just because it has Figment), the American Adventure, Kilimanjaro Safari, Expedition Everest, and TSMM.
In terms of the shows, we like: fireworks at the MK (any of the shows), IllumiNations, and Festival of the Lion King. (Disclaimer: I have not yet seen Rivers of Light, but that looks pretty good.)
As mentioned, you'll need to start thinking about dining (table service) pretty soon. ADRs open up 180-days in advance and the popular ones fill up pretty quickly. If something is fully booked on the 180-day mark, it probably means the folks with early access (those staying onsite) already filled up the restaurant (aside from the third party locations in Disney Springs, the restaurants do not hold out some of their tables for walk-ups). It's still worth checking because you never know when someone will cancel. Overall, dining in WDW is much more difficult than it is at DLR. Most CS locations are just like those in DLR (you walk up, place your order and the wait depends on the length of the line); the one exception is Be Our Guest (at breakfast and lunch) that requires/strongly recommends an ADR.
The other thing you'll want to familiarize yourself with is My Disney Experience (
MDE) and FP+. WDW relies much more heavily on their app. FP+ is similar in some ways to FP at DLR, but also very different. The
FP+ thread up on the WDW board is pretty helpful and worth a look.