Season 2 of The Simpsons, upon looking at it one more time, was quite possibly the most human and down to earth season in the simpsons history. It may not have been as polished as the golden years simpsons (seasons 3-8) in terms of animation or comedy, but the animation was a hell of a lot better than season 1 and the humour was still quite good.
However, my main focus is on the sheer reality of this season. Watching episodes like "Principal Charming", "Bart Gets an F", and "Bart gets hit by a car" among others made me realize that the simpsons, as funny as they were in the later seasons, never really revisited the kind of tragic pathos and moral dilemmas these characters faced.
I like this season because it was an excellent balance of humor and tragedy. These characters made you laugh, but made you care for them because you saw their vulnerabilities on display. Bart's a bad boy, but he hates being a failure. Selma is lonely, and Patty feels bad about stealing away her chance at love. I mean, the list goes on and on. Homer gaining his hair, Marge's dilemma between her loyalty to homer and breaking the law, etc.
But the maturity of this season can be seen with "Itchy and Scratchy vs Marge". The Simpsons were a very controversial series for the time, and THIS is how they responded to their enemies. Not mockeries or caricatures, but an insightful analysis over the morality (or lack there of) of tv and a thought-provoking issue over what can be seen as "art" and "filth".
I could go on, but i don't need to repeat myself. Season 2 was one of their best seasons because it was their most heartfelt season. Not too crude, not too zany, not too strange. Just the perfect blend of tragedy and comedy.