You might be able to make some decisions a month ahead of time... as far as whether or not this or that route is possible.
This link is for planning your trip a week ahead or a day ahead of what you are going to do. Save it. It will come in handy.
Weather Underground Road Trip Plannerplay with it well ahead of your trip. Learn how to use it. Set your departure date and then check departure times to get the best road conditions for that day.
Learn how to check it against wind, elevation and radar.
Elevation makes a difference whether moisture is snow or ice.
WIND does too.
using the link I gave you, you can make a careful choice whether to roll the wheels sooner or wait a few days... or even stay put a few hours to get better road conditions.