Oh, Bob's GI Bill was used for his own education in the '50s.
Bob, in my opinion, tried what he thought would be a successful path for Chris. He tried to make sure Chris was watched over (galpals), got him into PVCC and forced him to get a job at Wendy's. That all blew up within a few months. I think Bob then went and got the Tugboat because he knew he was aging and at least made an attempt to make sure his son would be minimally taken care of. Look at all the bullshit Bob dealt with by making Chris dig his way out of debt. But Chris never learned. I think eventually Bob simply gave up due to age, illness and an inability to get his spawn to listen and be responsible. Bob tried to provide for his family but, as we've seen, they managed to squander all of that in less than two years. For further evidence, watch the 2004 Christmas video. Bob's lack of fucks is pretty obvious.
As for the failed trolls, I imagine the learning curve has gone up significantly since 2010 while the weens' ability has not. I am impressed at the official looking Cease and Desist. That is one helluva document to fake. I can only wish I had the sort of time and desire to fake shit like that. Oh wait, no I don't.