My parents used to use AAA TripTiks to plan our trips. Granted this was decades ago in the olden days of paper maps, so I have no idea how good they still are, but apparently they still exist. Worth checking out.
I did a cross-country move about 8 years ago, and just planned each leg of the trip separately. I chose where I wanted to sleep, planned the route to get there, and then did the same for the next leg. There’s really no wrong way to do it as long as you connect the dots and go the way you want to.
I thought it was just me and my old iPhone, but I’ve also been having a lot of trouble connecting for the last few months. Since May, really.