Stravaganza/YMMV

Magnificent Bastard (Niccolo di Chimici. Silvia, the Duchessa of Belleza in book one, also qualifies as a female, protagonist version.)
Narm: Sky's dad's stage name is Rainbow Warrior. And this man is supposed to be an American rock star.
- Maybe he started performing during The Eighties?
- I suspect this is a reference to the Greenpeace Ship of the same name, which was famously bombed by the French Intelligence Service. It caused quite an outrage, and has been referenced by a lot of real musicians.
Tear Jerker (Lucien's Earth death in the first book - and the funeral - and Rodolfo's visit.)
- Luciano's brief reunion with his parents in City of Secrets.
The Woobie Many members of the cast qualify from time to time, but Guido from the first book deserves mention. He's hired to murder the beloved Duchessa of Belezza, a figure who is practically worshipped by the people as a demigoddess. Why is he committing this act of treason? Because his father is deathly ill and his brother squandered the family fortunes, so there's no money for medicine. Worse yet, Guido loses his nerve when confronted with the Duchessa and can't bring himself to kill her; he's spotted with the knife, tackled, and thrown into the equivalent of the Doge's dungeons. Ashamed and resolved to his death, he throws himself at the Duchessa's feet and begs her forgiveness before he dies. Silvia spares his life because he's so repentant and apprentices him to two of her former lovers ... after telling them that Guido tried and failed to kill her. Guido spends the rest of the books tailing Silvia and being her bodyguard/manservant.
- In terms of the main cast (all of whom have problems), the woobie award goes to Luciano and Nick, hands down.