Climbing and altitude hit a person pretty hard on a long ride like that one. What time of year? Now? MID SUMMER?

I did 300+ miles in two non-consecutive days last year, and did two consecutive long days about 20 years ago. It is certainly very possible to do. I was hurting the day after my 181 mile last year. Even 20 years ago when I did it, I took a few shortcuts on the second day coming home.

It depends a bit on if they are taking the guy to a bike shop, buying a new bike, then saying see you in 2 days in Vegas.... vs getting the bike and giving him a month or two for training and break-in. Ahh, according to the article, starting around May 31, so about 3 1/2 months... I'd say sure if he puts some time on the bike. He may even be able to do 2 attempts in may.... legal?

Looking at the route (and having driven in the south a couple of times), there is a pretty substantial climb coming out of LA, but that would hit one while the person is still fresh, both good and bad.

If I was doing the ride, I'd plan on riding in 1 day from about LA to Kelso (or so). That would be a very long first day, probably a bit over 200 miles. Then, sleep for 8 to 10 hours or so. Hop back on the bike for the final hill climb, then coast the rest of the way into Vegas.

I think it is very possible for an amateur rider to do. But, I'd hate to have a half a million bucks riding on it.

No sense not going fully supported (food, water, camping equipment, etc all by vehicle). MOTEL. Heck, one could hire a pro team to give draft support.