Welcome to the RTA forum!

From the looks of your plan, you've made several common mistakes in your planning.

First, the amount of time you are planning to be on the road is simply fantasy. Remember, online mapping programs assume you'll never have to stop, slow down, get gas, or do anything but drive non stop. This trip will take at the bare minimum 36-38 hours on the road - but in any case its a trip that needs to be measured in days not hours.

I think you are also really overestimating how far you can travel in a day and maintain your peak level of alertness. Leaving presumably after a full day of work, and then planning to drive until 1-2 am just isn't a smart way to get your trip off on the right foot. 12 hours a day on the road is doable, but that's a long day that leaves almost no extra time, and you'll generally cover about 600 miles in that day.

Simply put, there is no way that you can safely leave Winona on at 6pm on a Thursday and arrive in Southern California on Saturday. Quite frankly, if you planned to arrive late Sunday, you'd be pushing things and would have nearly no time for stopping.

You've also made the common mistake of assuming weather along I-40 will be better. The route you've selected frequently sees ice storms across the southern plains, and crosses several mountain passes above 7000 feet through New Mexico and Arizona that can and do see snow. There are many times that I-80 or I-70 are better choices, but that depends completely on the actual conditions and forecasts. The fact is any of those route could see a storm that could force you to slow down or even stop for a day.

Its not going to be impossible to do this trip and have a good time, but I think you really are going to have to rework your expectations, and understand that more realistically you're only going to have about 2 days in the desert based on the amount of time you've told us you have to work with and the kind of trip you want to do.