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 only commit atrocities because just follow orders. Or he is a Psycho for Hire? Toni is probably the protagonist who committed the greatest atrocities canonical, including killing a man with an ax and carrying his remains to a butcher shop, and this was done intentionally and not to follow an order, without mention several atrocities that go by Donald Love and Ned Burner's orders. While still repents of his sins in a confessional, he never sought redemption when he bombed the area of Fort Staunton.
Donald Love certainly qualifies. While Grand Theft Auto III only vaguely alludes to his monstrous tendencies, Grand Theft Auto: Liberty City Stories sheds some light on his true personality. He will truly do anything to make money, including having Toni murder his mentor Avery Carrington just to steal his plans, as well as a news reporter that witnessed the murder. Did I mention what he does with the bodies? His most monstrous moment is when he orders Toni to sneak underneath the Fort Staunton section of Staunton Island and blow it to smithereens, likely causing the death of thousands of people. This action also explains the existence of the construction site in GTA3.
That reporter you mentioned weren't a saint either. Ned Burner, posing as a priest in a confession booth, got Toni (who was seeking redemption for his sins, ironically) to wreak havoc on the streets in a fire truck (killing countless civilians) so he could be the first on the scene to write a scoop about it, kill 3 celebrities who gave interviews to rival media institutions, kill a federal witness to a doping scandal and pull off a diamond heist. Damn, Toni Cipriani probably commits the greatest canonical atrocities of any GTA protagonist to date thanks to the orders of these two men.
Moral Event Horizon: Paulie Sindacco intersects with the attempted murder of Salvatore, sending his henchmen to take him to the crusher.
Toni's mother has probably crossed with the attempted murder of her own son for not being a man.
Nightmare Fuel: Several thing that makes Toni Cipriani is 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 if unhelpful.