So I decided to record my first playthrough as Tuscany (my usual go-to for testing out new mechanics).
Matilda di Canossa (d.1101)
Matilda di Canossa inherited the Duchies of Tuscany and Spoleto on the death of her brother, Federico I. She matrilinially married Hugues d'Ivrea, a descendant of King Adalberto I of Italy. Renowned as a skilled and pious diplomat, she was well respected as the family matriarch. On her death of old age, her realm was split between her two sons, with Federico II gaining Tuscany and Emilia and Bonifacio III gaining Spoleto. Hugues, the Dowager Duke, would outlive her by three years.
Federico II (1101-1136)
Federico II inherited Tuscany and Emilia, and would later name himself Duke of Ancona as the western lords swore allegiance to him. He married Serhilda von Rheinfelden, the daughter of Duke Rudolf of Swabia, who would outlive him by 19 years. Federico would soon eclipse his mother in fame, fighting in both of the Crusades. Both times he his sister, Stefania, and convinced the pope to name her Queen of Jerusalem. He was also devoted to his wife, and became renowned as a paragon of chivalry. He was well respected enough that his eldest child, Adelaide, was able to marry the King of France, and his third daughter, Serhilda, married the future King of Galicia, so Federico is known as the Brother and Father of Queens. While wounded on the Second Crusade, he died from advanced age near Antioch, dividing the realm between his three sons Ugo II of Tuscany, Federico II of Emilia, and Rodolfo of Ancona (later King-Consort Rudolf of Bohemia)
Ugo II (1136-1176)
As a young man, Ugo was married to his kinswoman Agnes von Rheinfelden, the heiress of Swabia and, more importantly to the Italian Federico, Lombardy (her grandfather Berthold was Serhilda's brother). During their marriage Agnes produced two children - Bernardo, named in honor of King Bernard of Italy, and Benhilde. However, Agnes died in 1134 at the young age of 22, and so Bernardo became the Duke of Swabia and Lombardy, while Ugo remarried to Sarrazine Noailles, the Dowager-Countess of Lienz. While she already had a son, Count Rapoto von Friedenthal, and a daughter, Guntrud (later the Countess of Nottinghamshire), it would be Sarrazine who would give Ugo his remaining children - Ugo, Serhilda, Federico, and Sarrazine. Ugo II was cut from a different cloth than his father - a ruthless, arbitrary schemer of a man who saw nothing wrong in routinely killing opponents and threats to the Canossa lineage, although he drew the line at kinslaying. When the Sardinian rulers apostated, he moved in and seized the island from them, naming himself Duke of Sardinia (he could have named himself King, but desired that Italy would be his family's first royal title, referring to his son as "Bernard II" in private writings). When physicians informed him that Benhilde was unlikely to have children, he simply gave her to a convent with little fanfare. When his brother-in-law Munio apostated, Ugo arranged for him to be killed. When his successor and grandson Lourenzo also apostated, Ugo had him killed too, leaving the throne to the zealous King Vela. Tragedy would strike Ugo, first with the death of his wife Sarrazine in 1167, and then, the following year, the death of Ugo the Younger in battle during a war to protect Bernardo's inheritance. Ugo would eventially remarry - to his mistress Silvana, a former barmaid - but Ugo the Younger's death would haunt him, and he died of old age, splitting his patrimony between Bernardo and Federico (Who inherited Sardinia).
Bernardo (1176-1195)
Bernardo, a quiet intellectual, was doomed to have an unfortunate life. His first wife, Marijana, died shortly after their marriage, when he was only 16 and she a youthful 40 (his father would annoyingly change the subject whenever she came up). His second marriage, to Andela of Cedynia, was slightly more succesful, giving him two sons, Ugo and Cosma, but during their marriage he lost Swabia to a war against his own great-aunt. After unifying Lombardy and Tuscany, Andela was suddenly murdered, with his own son Ugo being the most likely culprit. Still, Bernardo tried to see his father's dream of the Canossas becoming Kings of Italy to the end. He managed to force Emperor Gausbert to recognize the independence of Lombardy and several other petty realms. For companionship, he married Sarrazine Reginar, who had been twice widowed and already had four children and was unlikely to have any other (although, as a pious woman she would state she only had three children - her eldest daughter had fallen in with the Adamites of Valentinois). But the tragedy of Bernardo wouldn't end. After a short war gaining Polesine, Bernardo set his sights on Lombardia, the theoretical seat of his domain which was held by the loyalist Duke of Genoa (when the Rheinfeldens inherited the Welf lands, Rudolf gained Lombardy and Corsica, but for whatever reason his brother Engelbert gained Lombardia proper in addition to the Duchy of Genoa). This war would prove to be an unmitigated disaster - for six years Bernardo's forces would seize Milan, only to be beaten back by the numerically superior Imperial armies. When his son, Count Cosma of Brescia, was killed by Count Lothar of Breisgau, and a botched treatment left Bernardo himself castrated and on death's door, his heart went out of the fight. Bernardo used his position of strength to gain a white peace, then died, leaving all lands to Ugo (except Brescia, which had been inherited by Cosma's daughter Fortunata).
Ugo III (1195-?)
It is unknown what the future will hold for Ugo III. Like his father, his first wife had been a considerably older woman, the widow of Bonifacio III of Spoleto's grandson. When she died , he married a lowborn woman named Ginevra, who was again older than him (although in this case only five years older instead of twenty-six like Libuse had been). Still, Ginevra has given him one child, Ugo, who will likely become Ugo IV in his time. A fickle and impatient man, his father's tragic life and death have nonetheless given him pause on the family ambition to gain Italy. Maybe a Third Crusade will be called and he can rebuild the family influence that way, but the second fall of the Kingdom of Jerusalem seems to have killed enthusiasm for those. Regardless, it is clear that the lineage of Alberto Atto of Modena will bottleneck soon, with the Ancona, Spoleto, and Emilia branches having formed their own houses and the Sardinians likely to follow. But that is for the future to decide.
With Bernardo's death I decided I had a good run with this playthrough. I was never able to become King of Italy, but seeing the ups and downs of the family was definitely a fun experience.