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.
Toni Cipriani: a righteous man who delights in only committing atrocities because he just follow orders. Or he is a Psycho for Hire? Toni is probably the protagonist who committed the greatest atrocities in the GTA canon, including killing a man with an ax and carrying his remains to a butcher shop. Remember, this was done intentionally and not to follow an order, not to mention several atrocities that go by Donald Love and Ned Burner's orders. While he still repents of his sins in a confessional, he never sought redemption when he bombed the area of Fort Staunton.
Complete Monster: Donald Love somehow manages to reach a special level of evil despite living in a Crapsack World populated with gangsters, serial killers, and psychopaths. Introduced in Grand Theft Auto III, Love at first seems fairly standard for the series, arranging a gang war between The Yakuza and The Cartel just to lower property values. Though, at the time it was hinted he had more sinister appetites. This is eventually confirmed in this game, where he's shown feasting on corpses and sending Toni Cipriani to collect bodies for him to devour. Aligning himself with the Leone crime family, Love runs in the race for mayor, sending Toni Cipriani out to murder his rival's campaigners. Losing his fortune in his failed campaign, Love makes plans to regain his fortune, with his first step being to murder his mentor, real-estate tycoon Avery Carrington, in order to steal his city development plans. He then has Toni recover Carrington's body to cannibalize later. Love's worst crime, however, is masterminding the deaths of thousands of people through the bombing of the heavily-populated Fort Staunton city district, just so he can make money off of redeveloping the district. A thoroughly depraved man, Love would stoop to any low imaginable to fill his pockets or glorify his ego.
Moral Event Horizon: Paulie Sindacco intersects the horizon with the attempted murder of Salvatore, sending his henchmen to take him to the crusher.
Toni's mother has probably crossed the line with the attempted murder of her own son for not being a man.
Nightmare Fuel: Several thing that makes Toni Cipriani pure Nightmare Fuel. This is evident in the mission "Dead Meat", where he kills a man with an ax and dismembered him, and takes over his remains to a butcher for his remains to be sold.
That One Level: The game ramps up the difficulty for obtaining some of the hidden packages to an almost insane level. A hidden package located on top of a gas station roof in Portland is considered particularly difficult to reach, and even Guide Dang It assistance is unhelpful.
Vincenzo, who is heavily implied to be Green-Eyed Monster. At first, it's ambiguous whether he really set Toni up to be arrested by police or not, causing Toni to be pissed off at him and crushed his car. Then, because of this, he tried to kill Toni. He failed.
As if she wasn't bad enough in GTA III, Maria is worse in this game. Some of Toni's problems are because of her screw-ups.