It’s almost certain we’ll be making a habit of this kind of trip. In the interest of educating our future selves, here is a list of points to remember. If it helps you out in planning your own road adventure, all the better.
Keep a good balance of planning and serendipity.
We are notorious over-planners, and this trip was no different. Fortunately, we were cognizant, as were planning, to give ourselves room to move. Next time I would do it even more. What I recommend is to chart out a route, research the hell out of interesting places on your route (lean heavily on Chowhound and Ask Metafilter), keep a list of them with you, and then here’s the key: use it as backup, not as an itinerary. There will be days when you’ll need that list, but you should fully expect to find new and even more interesting places as you travel.