significant potential problems
Welcome to the RTA Forum!
I see several areas that look like they could be big problems.
To start, visiting Cuba and then Miami is not an easy transition. Because of the embargo, you will likely either need to fly to Mexico or Canada, and then take a connecting flight. There may be some charters, but you won't find any regular air service between the two.
The onto your driving, It looks like you've got some impossible legs.
You didn't say where in "Florida" your villa is, but you need at least 2 full days for the drive to New York.
The most concerning element, however, is your Chicago to Grand Canyon section. Even without any extra stops, you need a minimum of 3 full days for this drive, and it looks like you've only got 2 days planned, and that would include your actual time at the Canyon. That's just not possible.
Perhaps I've misread your plan, but that's going to have to change. I'm also a little curious about your plan to camp at the Grand Canyon. When you factor the cost to buy even basic supplies, camping for just one or two nights will cost far more than just staying in a hotel.