Many times... I made my first long-drive from Los Angeles to Portland, OR when I was 17 or 18. I drove the 990 miles in 21 hrs, and no problems. Many stops, because I had a 1984 Chevy truck with a big V8 and small gas tank, and I have a small bladder too. My longest drive in one shot was from San Antonio, TX to Ventura, CA in 23 hours (counting a 2 or 3 hour nap at a rest stop). I like the independence of road travel as compared to air travel, especially with the TSA and their "everyone is guilty of terrorism" attitude, and the probability of catching all kinds of bugs from other passengers.
As long as I carry enough cash in case of emergencies, and am not driving a vehicle with known problems, I love driving on long road trips
Charles