Between 1987 and 1991, I rode a 85 Honda VFF700F back and forth from Charleston, South Carolina to Houston, Texas on 3 separate occasions. Thus, you can say I have done the 1,000+ ride 6 times. (Well, 5 times actually. There was this one time when I was going back to Charleston from Houston and I nearly froze to death in Alabama. I had to leave my bike there at Fort McClellan and come back and get it in the spring.)
The speed limit back then was just 55 MPH. One time, I made the trip in 18 hours and 15 minutes. That was a straight run. No rest stops. Just stopped to stretch, get gas, take a piss, get a drink and then get back on the rode immediately. I was all impressed with myself back then. Now, I think it wasn't so smart. I am still proud of it though!
The very first one was the hardest because I had no idea what I was getting into. I recall wanting to back out and go back to where I started after just a couple hundred miles.