The sad/crappy part is that I'll have to continue to work full-time while we're away. (Ok, hold your sympathy- I get that this is an AWESOME opportunity!) Because of my work schedule, we'll essentially have 2 weekend days for our site-seeing. So, while it sounds great to "have a week at each location", the reality is- it'll be an accelerated visit each place.
We've decided that we are ignoring the north east and east coast, because we can do these in the future. So it cuts down on some of the places that we need to go. It was still very hard to map a route out that hits as many states as possible, gets us a flavor of each location, and doesn't miss too much. We have 52-60 weeks from the end of one school year to when my daughter would need to go back to start school on the first day.
I've started mapping the route out- starting with a Disney World vacation at Fort Wilderness, going counter-clockwise, first north and crossing the country, heading south down the coast and returning to Florida for our first winter (getting some more Disney time in!). Once spring starts to spring, we'll head back out going clockwise this time, from Florida to northern Alabama, the whole way to Death Valley and Yosemite and then bouncing around like a ping pong ball to hit the Midwest.