I say if you are seriously thinking about it, do it. You won't know until you actually drive what it is like.
Dh and I drive many times before we were married to car shows in his 2 seater car. We live in CT and the farthest we had going was St. Louis but Nashville/Pontiac,MI were pretty close to far. And we drove to Ohio, Louisville, Indy, etc....
I actually loved the drives.....back then. We would stop for gas and that is when you went to the bathroom and if it was meal time we'd eat/I'd grab lunch from the cooler. And a few times we stopped for the night.
Again, it was fun, we had no Internet (I don't think anyone did then) but we did have a
AAA book with a list of hotels and he had his mobile phone. Te kind attached to the car!
We drove to myrtle beach a few times as well and figured how bad could the drive to Ft. myers be, right?
Well my kids were great. The ride other then some traffic south of DC/north of Richmond was great but....driving thru the tree lined roads of NC and the long states of VA & SC were not fun. There were little to no cars driving down so it made the drive longer. The way back the snowbirds were coming home so it went by quicker to see constant cars.
Anyways, we decided that we couldn't do that drive again. Day 1 we left at 6am and stopped in santee, SC at around 9:30-10pm. Finally got to sleep and left the next morning at 6:15 and arrived at my sisters at about 3:30.
So we are going to try the autotrain next April vacation. Current flights are comparable to the price of the AT but it doesn't include a car rental, parking at the airport or a limo to the airport.
So we will see. If we hate the train, we can fly in 2015...