I would be looking for WiFi roaming agreements or national chains that offer free WiFi and route myself near by.
My last cross country excursion (via motorcycle) was over 15 years ago. Well before connectivity. I had a health club membership that belonged to an international organization that honored members who were outside a 50mile radius of their home club.

I mapped out member clubs along the way as well as 24 hour PathMark markets and was good to go. Slept by the pool during the day and traveled at night.