This episode seemed very uneven, and lacked much relation to "classic" Simpsons. It had some interesting tangents that could have been explored more deeply, but somehow the writers completely missed the boat.
We are introduced quite early to one sub-plot: Homer the expert breaker-upper and founder of Sweet Conclusions. While his interaction with Skinner was somehat entertaining, and his opening statement to Lenny's girlfriend Doreen was nearly classic, at the end of the day, there was no point in even introducing this concept as it didn't seem to go anywhere. It culminates in a Christmas Carol-esque dream sequence starring the Spirits of the Relationships [Homer] Killed, the Babies Those Couples Would Have Had and the Antiques Those Couples Would Have Bought Together. This sequence lacked any real clarity or direction, and made for the most un-Homer-like moment in recent memory: Homer changes his mind about something he has cared about for a short time. End of sub-plot.
A second sub-plot, the cruciverbalist Lisa, has glimmers of some of Lisa's finest moments -- including competing and relating with adults on a level playing field -- but has none of the lengthy conflicts that usually confront her interactions with her family (à la She of Little Faith or Lisa the Vegetarian). Her day-dreaming about words is a little too straight-forward, and could have been executed much better. The fact that Superintendent Chalmers is a fellow crossword enthusiast was somewhat out of character, and his yelling of "Skinner!" and "Skimmer!" were cheap ploys by the writers. The Citywide Crossword Tournament shold have been a great opportunity to install some classic Simpsons moments, but, alas, except for a rather bland Tribute To Words That Have Been Removed From The Dictionary In The Last Year, and a rather slick Gil Gunderson (he wins?!), the entire sequence was much too rushed. The betting Homer sub-sub-plot was perhaps perfect, but a little too trite.
Upon finding out that her own father had bet against her in the final, Lisa decides to take her mother's maiden name: Bouvier. This is an idea that could have been worth an entire episode, but somehow only comes up in the final five minutes. A very quick resolution of this turn is had (aided by a quite good Homer brain monologue), and we are magically back to square one, except I'm thirty minutes older.