Your instincts are usually right.
Hi Gregg, and Welcome to the Great American Roadtrip Forum.
You sound like a very level headed young man who has thought things over. I am impressed with your list of cons, as most young people would ignore and dismiss those concerns.
My only advice would be to go with your gut instincts. If you don't feel right about something, especially about others driving your car, then follow your inner feelings. They will always lead you to the best decision for you.
Lifey
Yep, the little voice inside your head knows best.
Stepping a little out of your comfort zone is sometimes the only way to discover new things. I think the main issues you need to address is whether you have the time and funds available to make it an enjoyable trip, if not I would wait until you do. Also keep in mind that if you are using an electronic mapping program to use for travel times it's likely to be at least 20% longer to complete the journey. I agree that you should go with your gut instincts as to whether some one else should drive your car, and although taking more people reduces the costs, it can lead to more distractions, such as fooling around or higher chance of 2 of the group falling out and causing tensions.