A self driving car wouldn't have to work very hard here to do better than me.
* Check for weather conditions at altitude (not just start and destination points).
* Refuse to leave the house using that route if weather conditions are bad.
Oh well, lesson learned. On that topic does anyone know of maps software that does that for you -- i.e. check weather not just traffic?
--
"Take me to the ski resort, HAL."
"I'm sorry Dave, I can't allow you to do that. It's snowing along the way."
"Yeah, I know--that's the idea. I want to make some fresh tracks."
"Driving through the snow would be more dangerous than driving on dry pavement. In addition, I calculate that skiing is 4.76 times more likely to result in injury than reading a book. Please return to your couch; I will download a new book to your Kindle."
--
Incidentally, this was a major theme of Asimov's Robots/Foundation series--that intelligent robots programmed to prevent humans from coming to harm would become nannies of humanity in order to execute that command.
Jack Williamson went to town on that. "With Folded Hands", a story later expanded into novel(s). Before Asimov, if I'm not mistaken.
That said, if you're much older than the first time you gave it a try, you might consider trying again. I've found that some boring books were actually fascinating when I tried again years later. My tastes have changed considerably over the years, even within science fiction.
When I use Google Maps to check routes, on my desktop or on my Nexus phone, it provides National Weather Service weather advisories along with my route directions. (I live in Minnesota, where those are presumably more frequent than they are in most parts of California.)