My brother and his son recently took this journey, only from NC to San Jose with a stop in Denver. It took them four days to complete it. If you are planning to take the trip alone, it may take longer.
My recommendation would be to invest in a AAA membership, if you don’t already have one. It can provide you with guidance, maps, and car emergency support if needed. It also might be worth looking into renting a GPS. Not only can one guide you, but they have the ability to pull up hotels, restaurants and local attractions. Plus, it’s like having someone else in the vehicle with you. :)
As for safety, it is just a matter of logic, preparation for dealing with the worst, and instinct.
When it comes to where to stay and eat, I use Trip Advisor. It lists hotels, restaurants and attractions by price and reviewers’ ratings. Unless the trip is time-sensitive, it may not be important to book hotel reservations in advance. If you do, make sure to note the confirmation number and cancellation policy of the hotel. The locals often give the best recommendations on where to eat.
Good luck with your journey. Please keep us posted on this adventure!