I use it all the time, but it doesn't execute on every step.

That's disappointing on the gdb front. Maybe there's a vim plugin.

How does someone graduate with a CS degree without understanding pointers? How does someone get a programming job without understanding pointers?

These are serious questions. They have to go through job interviews, right?

I work with people with CS degrees whose eyes glaze over when I talk about pointers

Is this a joke?

Also, is there any way to make gdb display several lines of code around the line of code it's currently executing? Automatically printing variable values would be great, too, but that's somewhat less of a concern.

I would think that for the majority of programming, decent-but-not-great is good enough. After all, programming is mostly about solving people problems, not computer problems, and the hard computer problems are already solved by the 10 year / 10,000 hour experts.