Hi, I've been out of it for a couple weeks, but I just noticed that
@Tyggress tagged me in this thread. Looks like you found my trip report... I'm about 2/3 of the way finished with it. Without rehashing the TR, I can only say that it was a trip of a lifetime. Truly amazing sites all the way! I'm sure you'll have an amazing trip if you do it!
I used a combination of Road Trippers, roadsideamerica.com, Google, Yelp, and Trip Advisor to plan the trip. I found Trip Advisor to be the most helpful, as they have forums for major cities and destinations, as well as ratings and reviews for attractions. You can learn a whole lot from lurking on those Trip Advisor forums.
To figure out where we'd stay each night, and what attractions we might hit along the way, I plotted everything out on a Google map. You can enter a starting destination and ending destination and it will tell you how many miles are between the locations and how long they think it will take to drive. For example, they said driving from St. Louis to San Francisco is about 30 hours without stops. We first planned to do the trip in 3 days, which could be 10 hours each. So, I started in St. Louis and plugged in locations that were about 10 hours from St. Louis. And then, 10 hours from that. And then we played around with the time zone changes and seeing what would happen if we left a little earlier. Etc. Eventually, we decided that we wanted to spend some time in Marceline, MO on the first day, so we broke it into 4 days. But ultimately, I used Google directions to figure out where we should stay each night. Then I looked at Trip Advisor for good hotels at that location. If there were two or three cities that might make a good stop for the night, I used Trip Advisor to help figure out which one would have better/cheaper hotels and better food options.
Once we had the skeleton route in place, I then used things like Road Trippers to find interesting roadside attractions and stuff along the way. This is an old version of the Road Trippers map, but here's an example of one of the maps that I used to track what we wanted to see:
https://roadtrippers.com/map?a2=t!4821195&lat=35.79999&lng=-105.71045&utm_campaign=trip&utm_medium=share&utm_source=copy&z=5
And again, I used Google maps to help figure out what time we might arrive and how much time would be reasonable to stop there. (For example when we stopped at the Golden Spike Tower in Nebraska on the way out, I had a pretty good idea of when we would arrive and about how much time we could spend without arriving at our hotel too late that night.)
On our way out west, we headed north and traveled along I-80 to San Francisco and then headed south to Anaheim. On the way back to St. Louis, we came back on 40/44. Without a doubt, I found 80 to be the better, more interesting drive. But we did make a few interesting stops on the way back, and it was a lot of fun seeing some of the Rte. 66 sites since we had just visited Radiator Springs a couple days before.
I'm sort of typing in a hurry, and I'm not sure if any of that made sense, but feel free to ask any questions that you might have about the trip. And of course stay tuned to the TR for all the stuff we saw on the way back to St. Louis from LA. Even though I liked I-80 better, driving through Arizona and New Mexico was incredibly awesome too!