Well, this is a tentative schedule. I haven’t finalized an itinerary yet, and some destinations will probably get dropped due to timing. I do also plan on at least one or two alternate itineraries in case, e.g., a snowstorm rolls across Kansas and Colorado, I could veer south towards Texas. I also could request more PTO, but I don’t want to use up everything in the first month of the year.
I can't know your circumstances, but I would rather take the PTO for this trip in summer. There are many reasons. Driving in winter is more dangerous even if you know the route. On some days weather may be just too bad to drive safely, and it's too late to change the course. Then you won't see much in places where snow covers the ground. Then you need to carry clothes for all kinds of weather, considering that you will be all over the place, and a winter survival kit. So if technically you can get from point A to point A through point Z, it won't be much fun.
You probably also need a set of chains too, unless you are very sure that you won't find yourself where they are mandatory.