We were scheduled to sail during 130 mph Hurricane Jeanne in 2005, and were not treated well by
DCL. We had a similar plan, fly in for a few days at WDW, then the cruise. They didn't cancel the cruise until after we had already gotten on our flights! It was extremely frustrating because we flew into the path of a major hurricane and then DCL said "never mind". We couldn't even get anyone on the phone because all the CMs were in the Orlando area. They provided no help with lodging whatsoever.
Mercifully the folks at Animal Kingdom Lodge were incredible. We extended our stay through the length of the cruise, the parks were nearly empty for days afterward, and it was my favorite WDW vacation ever. The Lodge never even lost power, the restaurant was open, it was really a great job done by the resort folks. The cruise did leave a couple days later, from Port Everglades down in the south of Florida, with an abbreviated itinerary. We just took a refund. That said, it would be foolhardy to knowing fly into the path of a category 5 storm, even one that is likely to be significantly weakened by landfall. Disney is incredible, Jeanne had 100 mph winds when it reached Orlando and the parks were open the next day. But you never know with flooding, etc.
My tips: 1. Book in a deluxe resort, the "intermediate" resorts are really motel style, and people were confined to their rooms. That would have been a drag. 2. Don't assume you will be able to contact DCL, or get any help from them.