Kevin Jackson is bald because he was Embraced with his horrible "Kid and Play" haircut from the 90s. So, he'll be stuck with it for all eternity unless he shaves it every night (and almost certainly does so).
Bobby Weatherbottom being an Anarch makes sense not only because of the rise of hacktivism but the fact the Red Question was a major Anarch group in V20. It's all but stated that he was a member of said group in Anarchs Unbound.
Kevin Jackson's rise to power makes perfect sense if you note that the events of V5 mean that a large number of very powerful Elders were taken off the table due to the Beckoning. His natural rivals were also neutralized with Ballard being humiliated by Son via blackmail, Al Capone becoming a walking Masquerade breach due to the Second Inquisition's rise, Juggler's attempted coup failing, and Dusable suffering PTSD from the events of Blood Treachery. As one of the few competant members of Lodin's brood left, it's honestly insulting Joseph Peterson got the nod before him.
Damien defecting to the Camarilla makes sense with the fact that his Anarch friends were mostly killed by Garou, not the Camarilla, and his greatest enemy (Balthazar) would lose his position as Sheriff. Gengis, his only other close Anarch friend, was covertly supporting Kevin Jackson too.
Anita Wainwright becoming Baron of the Chicago Anarchs makes sense as Joshua Tarponski left to become Baron of his own city in The Chicago Folios, Juggler was disgraced, and Maldavis continues to be in a funk. She was always The Heart of the Movement in Chicago and simply moved to a more direct role as leader.
Ballard's destruction of the American steel industry means that the entire economic collapse of the region is his fault and he could do it to other industries at any time.
Bobby Weatherbottom's horrific treatment of his girlfriend where she's kept in a medical coma and milked like a cow shows how even an otherwise "nice" vampire due to his Ventrue feeding restriction can be ruled by the Beast.