These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Harsher in Hindsight: The second Imagine Spot at the ball game, where Gil imagines his son as a clock tower school shooter. It's played for both drama and comedy (comic in the sense that Gil is obviously imagining an over the top, absolute worst worst worst case scenario), but with how (relatively) common school shootings are perceived as being today, it pretty much eliminates the comedy.
First, we have Steve Martin as Gil. Gil is a loving father, but he believes that he isn't good enough, which takes Martin's trademark irritation and misanthropy into some very dark places.
There's also Rick Moranis and his portrayal of Gil's brother-in-law Nathan. All Nathan wants is to raise a prodigy, but his Super OCD is not only Played for Laughs in this case, but also Played for Drama when he attempts to keep things orderly with Susan, his wife and Gil's sister.
And we can't go without mentioning Keanu Reeves and Tom Hulce as Tod and Larry respectively. Yes, Tod is basically Ted with one letter in his name changed, but does so with grace and pathos, and really delivers one of the defining speeches of the movie and shows Tod's Hidden Depths subtly but clearly. And while Tom Hulce already had an Oscar nomination to his name, his performance as the perpetual but sadly aware family screw up Larry shows real depth.
Family-Unfriendly Aesop / Unfortunate Implications: In an episode where an aspergers child has to learn to apologize with the help of a teacher regarding his getting into a fight, the teacher showed him a tape of someone apologizing for something he did so he'd have a way to emulate how to apologize. The video she showed as the model was when Bill Clinton had a public broadcasted apology shortly before the Lewinsky Sex Scandals and Clinton impeachment hearings came about, which alongside the issue of whether Clinton was actually sincere with his apology, carried the implication that the teacher was essentially teaching the kid to fake remorse and deliver a unsincere apology.
The Woobie: Judging by his politeness for a 14-year old boy who has been though parental abandonment and all sorts of nasty hardships, his reactions to awkward family situations, and how the audience plain loves him, Drew is fitting this trope to a T. The audience continues to beg for more of him every episode.
Mr. Cyr as well, given Sarah's treatment of him since his introduction as a love interest and the recent re-appearance of Seth. bordering on a concerted effort to Break the Cutie.