Orlando: it's where Dan lives now. Toasty weather, lots of touristy diversions, about an hour from the Gulf or Atlantic Ocean, decent downtown nightlife, booming population. However ... very suburban in character, few cultural amenities, not much history, very transient population, toll roads everywhere, more than its share of Confederate enclaves (coughWinterGarden coughcoughBithlo coughSaintCloud), tourist-based economy, and no topography.
Kansas City: it's where Dan is moving to. Great urban neighborhoods, interesting history, interesting landscape, fantastic cultural and urban amenities,Country Club Plaza, good schools, and a more rooted population However ... scary weather, no large bodies of water nearby, more urban grit (some might see that as negative), nation's largest freeway system relative to population, Missouri dysfunctionality, risk of Sprint pulling a Worldcom.