We have been to WDW many times and love it. Along with all the other advice, I would make sure you pick up a map of each park as you enter; that way you can find all the smoking areas where you can have a cigar
Sosa's is overpriced but the selection isn't bad and they actually made some nice sticks themselves. FWIW, I believe that Sosa and AF share a factory... Mostly I bring my own sticks, but I still like to browse and find something new to try.
Sosa also has a little cigar bar in what used to be "Pleasure Island", it is also expensive and has a much more limited selection of cigars, but it's a nice place to visit while your family is shopping.
We usually stay at WDW resorts. This can be more expensive on the surface, but Disney provides all the transportation and being closer to the parks you save some time and money that way too. It's all a matter of perspective.
As Scott said, make sure to get a parkhopper pass -- it's the only way to get the most bang for your buck in terms of tickets.
Do a little planning. Some rides are harder to get on than others. When you first get to a park go get a fast pass for the busy rides (Soarin' in Epcot, Toy Story Midway Mania at the Studios, etc.). Then go on some of the other less busy rides while waiting for your fastpass time.
There are a lot of resources out there to help you -- Internet Forums, smartphone apps and books. Use them...
Oh, and have fun!