First cross country road trip - HELP

We all make mistakes. I suspect he learned a huge lesson about what it means to swing wide. No harm, no foul, just a hit to the pocket book. He will do better just like you did when you first started driving. As to planning, there is no need to plan anything and certainly not months in advance. I just need to know I can get from point A to point B by a particular date (like meeting you in BC on a specific date). How I get there is not important and plans often change, sometimes daily.