It's hard to define just exactly what is wrong with contemporary Simpsons episodes. There's little consensus on just what made them bad and when. What's not hard to see is the definite drop in quality between an episode from, say, the 4th Season to one airing currently. (When we say "bad" in reference to a Simpsons episode, it's important to note the term is relative)
For me personally, I can see the show slipping between the seventh and eighth seasons, but the ninth (1997-98) presents a definite display of everything that is bad. And it all starts with "The City of New York vs. Homer Simpson"
First Act Misdirection" trope. A standard of Simpsons writing that went from somewhere near "fresh and irreverent" to "really goddamn tired". Long story short, Barney is stuck as the designated driver for a night at Moes, Duffman shows up, Barney is pissed, Barney steals Homer's car and disappears for two weeks. Homer get's a letter from the city of New York, telling him his car has been booted in the borough of Manhattan.
Let me take the opportunity to say that I really like Duffman. I think he's funny, I really do. But he has never been in a decent episode, because he was created too late. The same goes for Gil's sad Glengarry Glen Ross pastiche. Hilarious, but poorly utilized.
Now we get to the real meat, the wholly inconsequential "The Simpsons are going to [Destination]!" plot. I hate this plot. A whole bunch. Usually the writers use it to shoehorn in irrelevant Guest Stars (a fate from which we are alleviated in this episode) and generally not tell us any story at all. Here we get that no story, and do we ever get it. Homer, it is revealed, had a bad experience as a teenager in New York (in one of the funnier moments this show, Woody Allen drops garbage on a young Homer).
Homer has to sit outside the World Trade Center (complete with now uncomfortable World Trade Center jokes) all day waiting for the traffic cop to unboot his car. Here we get to see
A) Homer choosing to drink an excess of Crab Juice as opposed to Mountain Dew (Take THAT Mountain Dew!)
2) Homer having to scale both towers in search of a public restroom, in the meantime...
•) Missing the officer and recieving another ticket.
And while all that absolutely nothing is happening, Marge and the kids are, what's this, DOING NOTHING? The rest of the family spends the episode "sightseeing" and milking whatever fresh and exciting gags they can from New York City. Homer eventually gives up and drives off with the clamp still attached to his tire. And the Simpsons leave New York.
That's it. So I guess what I really hate is the inconsequential nature of later seasons. But wait, I also hate the shallow character development (Think: sober Barney, married father Apu). So I'm left just a confused as I was before.
And really, I don't hate this episode, nor do I find it that egregiously terrible. In fact, the much reviled "The Principal and the Pauper" immediately follows this episode (an episode I similarly don't actually hate myself), and "Realty Bites" is also coming this season (easily one of my least favorite episodes ever, and oddly enough the first appearance of Gil). But let's face it, the Simpsons isn't good anymore, as if it hasn't been said enough for the past 15 years.