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.
Crowning Moment Of Funny: The candidates for detective evaluation scene in The Enforcer. Especially when Harry gives Kate Moore a hypothetical situation about Mrs. Grey (who is in the room) and a shetland pony.
Draco in Leather Pants: Averted in Magnum Force, John Milius might have suspected the audience could sympathize with the vigilante cops for doing away from some genuinely deserving scumbags, so he threw in a few scenes of them murdering collateral victims to keep that from happening. In the Ricca killing, the vigilante cop (who could be Davis, but also could be Astrachan, Grimes, or Sweet) executes not just Ricca, but also his driver, his bodyguard, and his attorney. The pool party massacre had a lot of collateral victims, many of whom probably had nothing to do with the organizer of the event. Davis's shooting of the pimp is probably one where you can sympathize for a few moments (because that man clearly deserved the full six rounds of a revolver after what he did to that prostitute). But in the Guzman killing, Davis not only shoots Guzman, but he also shoots two female hangers-on who were in the room with Guzman at the time, and in the getaway also ends up shooting fellow officer Charlie McCoy.
It also keeps Lt. Briggs from having a Strawman Has a Point moment when he tries to defend their actions later (since no, they didn't all deserve it).
Harsher in Hindsight: In Magnum Force, a pimp kills one of his prostitutes in a taxicab with a bottle of drain cleaner. Reportedly, the men who committed the infamous Hi-Fi murders in Ogden, Utah in 1974 had watched this scene numerous times, although when they actually tried it all they managed to do was cause an allergic reaction in their victims. They had to resort to shooting the victims.
Moral Event Horizon: Scorpio crosses the line when he gleefully shoots children, then keeps moving the bar higher and higher for despicability and brutality when he kills a young African American boy sniper-style (as though he were a member of an enemy army), kills a police officer (disguised as a priest), brutally rapes a teen-aged girl before leaving her to die in a shallow well, blows everyone away inside a liquor store, and then hijacks a school bus, slapping 10- and 11-year-old boys and girls around and brutally shoving the driver nearly out the door while the bus is in motion. Scorpio's final act is taking a child hostage and daring his pursuer – Callahan – to surrender, or the boy will be killed. This time, Callahan wins!
In Magnum Force, the vigilante cops cross it when they begin murdering innocent women hanging out with the criminals and Charlie McCoy. Bobby Maxwell crosses it within the first few minutes of The Enforcer, but really crosses it when he stabs an elderly night watchman in the back, then shoots a wounded underling.
Narm: The Dirty Harry franchise has had its unintentionally funny moments:
The mayor's assurance that Scorpio will not be "molested" in any way.
In an early scene in The Enforcer, when a criminal gang demands a getaway car, Harry gives them one: he gets in his squad car and rams the shop front where the criminals are holed up, taking them utterly off guard. In a later scene, Harry is chasing an assassin on foot across rooftops, who accidentally falls through a roof window - right into a porn film shoot. Harry also uses a toilet plunger on an underworld figure's face to extract information from him.
Sequelitis: General consensus seems to be that each film is successively worse than the last, although there are some who argue that Sudden Impact is better than The Enforcer was.
Strawman Has a Point: Defied in Magnum Force. It was known audiences would sympathise with the Death Squad, who were murdering genuinely bad people, so they had them murder a few innocent bystanders and hangers-on and a fellow motorcycle cop in the wrong place at the wrong time.