I'm not actually asking that Sterling be turned into a genius. I'm asking that he GROW A PAIR OF BALLS and stop allowing himself to be treated like a friggin doormat.
Speaking as someone who used to be bullied in school, and as a result, became paranoid about people's motives, that's actually not possible. If you're paranoid, you're too busy wondering about what the catch is, than to assert yourself. After all, that's how you put a target on your back. If you keep your head down, they don't notice you.
And Hunter has Sterling paranoid. Sterling is always on the look out for what Hunter is planning (and as a flaw is focussed on Hunter too much, so he doesn't catch on what Hunter has done behind the scenes). His family, on the other hand, can be trusted, and as a result isn't his focus. Because any effort he puts in being assertive with his family means he's not spending effort on keeping an eye on Hunter's scheming. If you're focussed on the horizon, you can't focus on your immediate surroundings.
And in case you're wondering, yes, I'm doing much better now.