I realize that you are talking about having more of an official list of places to stop, but thought I would throw this in. When I was travelling across the country for all my racing, I got quite a number of friends/fans along the way. I was invited to stop over at any number of places across the country to take a break, have a meal, and/or sleep for the night. Most of it was networking online and then meeting up with the people at the races, but there are a lot of people that are more then willing to help out. Especially if they think it is a cool thing that you are doing. I'm sure you could find a lot of people that would let your oportunity charge at their place even if they don't have an EV, just because they would think it was cool that you have one and are travelling across the country with it. It makes them feel like they helped to make it possible, that they are a part of it in their own way. I think if I put in a little effort in this specific goal, I could probably get enough people to come on board to allow me to charge at their place all the way across the US. Actually, maybe not. I just remembered that one stretch of I-10 in Texas where you don't see any form of civilization for hundreds of miles. We almost ran out of gas a few times through there. But besides Texas, I think it could be done.
I do like the idea of businesses adding charging stations, in the same way they offer hotspots. That was my first thought when I started reading this. Maybe a bike rack with some outlets on it, the same way they have outlets on the side of toolboxes now.