I've found #2 a pretty problematic part of education that I'm still sort of trying to unlearn. Once you realize that's what's going on, the goal becomes not to do things "for real", but instead to reverse-engineer the education system: figure out why the question is being asked, what it's designed to test, and what kind of answer it's designed to elicit, then answer accordingly. This often greatly simplifies the problem space, because using some heuristic meta-reasoning you can really narrow down what's "really" likely being asked and what forms the solution is likely to take (or even what methods the question is likely expecting you to use). But then that's a skill not easily transferable to "the real world" when working on problems that aren't specifically posed to test a particular skill or with a specific answer in mind. Though it's probably a good skill for job interviews.
I actually think #2 is more of a hacker symptom rather than limited to the weird Lisp Programmers. Someone here put it fairly bluntly a while back in the form of a "How to tell if you're a hacker" quick quiz. At the end the answer was something like "If you intuitively tried to 'game' the test, you're probably a hacker. If you don't even know what that means, you're probably not one."
I think it's a useful skill to sharpen and definitely not limited to passing tests. There are diminishing returns to worry about for how much you want to try and game something, but having even a basic intuitive feel for it is pretty useful in "the real world".
