I'm going to ignore all of the ridiculous comments in this thread and get right on topic.
We have tried something similar to this with wakeboarding. They only way we could make it work was to stagger the boats to create a constant Double-Up wake. It did work, but was inconsistent due to wind, PP speeds etc. But on the occasion we got the wakes to line up, it was stellar and hitting a D-Up wall like that running at normal wakeboard speeds was unreal.
I am thinking that this is how you need to run to get the wakesurf wakes to line up. Ours was staggered about 100ft in front of the boat with the rider and off to the side about 30ft (this should be the side the rider is on). The speeds have to be identical to get it consistent, but it could work for a short time. The front boat dies not need to have a weighted side, only to be creating a decent wake at slow speed.
Honestly to get this to work you need two good drivers that KNOW HOW TO READ WAKES, and how to drive them at angles so that you get the convergence.