Maybe not what you're asking for, but a tangent:
Make sure your systems are up for what you're asking them. Our rig worked perfectly plugged in at home... When we did the trip from NH to KY I found several deficiencies that made things very difficult for us, primarily battery capacity (still have to address) and the toilet (which we addressed half of pre-trip due to time constraints, other half post-trip).
Months before the trip, we did call a local hotel and asked them if they had any arrangements for park-and-stay. We found one a few miles from home that would charge around $15 per night to park in the corner of the lot. I would suggest conducting a similar exercise if you haven't already- it isn't enough to just unplug at home, leave your property.
More on point:
I think what you need to do is ensure is that you have a place to park wherever you plan on going. I don't think anyone can tell you where in the country you should go. I think you should try making arrangements of where to stay, be it friends, family, fellow skoolie members... Then try executing on that- plan the trip. How many hours you will drive, what hours you will drive, where you will stop. How to caravan if multiple vehicles. Try to do a mini trip, maybe a state or two over, where you will return prior to your 5 month launch window so that you can correct for any issues before you "hit the road".
You can't have enough practice, or gain enough experience. I've learned things, corrected for mistakes, and I'm sure I'd find more mistakes if/when we move again.
Best of luck.