IMO, you can wakeboard easier in a little chop. As I've gotten older (52) a little chop is OK on a ski but not nearly as much fun as smooth water. It seems less tiring and easier to link turns, etc. on a nice, calm water run. I guess what I'm trying to say is that the conditions can also impact how you feel and maybe how much progess you can make quickly.
I can't speak for everyone here, but I can't stand it when the driver doesn't hold a straight line. Again, it doesn't bother me so much on a wakeboard, but on my ski even a little deviation by the driver makes me crazy (unless of course, they have to change direction for safety). Have your driver pick a point and hold a straight line to it - signal when he needs to turn - and then have make a run down the opposite way. Anyway, this is the way my wife and I drive for each other.
I hope to get to Coble next June as a Father's Day gift