Harry Potter...ages 17 through 36
1) "Harry Potter and the Bottomless Cup" -- Details Harry's drinking problems in his college years
2) "Harry Potter and the Therapist's Couch"-- Harry gets back in touch with his feelings about the war and the loss of his parents with the help of a middle-aged Italian therapist with good legs (and doesn't die at the end).
3) "Harry Potter and the Blue Stones" Harry's life given that Ginny Weasely is not ready to move on from "snogging" to more advanced activities.
4) "Harry Potter and the Big Fat Witch Wedding" -- Marrying into the Weasely family means learning about the dark side of Ron's Mom and Dad via planning a complex wedding that only mixed-bloods are allowed to attend (special scene involves Hagrid, a punch bowl of scotch, and a toast invoking the word "wand" several times at the reception).
5) "Harry Potter and the Post Partum Depression" -- Harry struggles to keep Ginny from drowning her first child.
6) "Harry Potter and the Quarterly Report" -- Harry finds that his reputation doesn't help in the business world. Learns important spells including "Anus Osculatus" to be a large help.
7)"Harry Potter and the Seven Year Itch," It turns out that new young witch in accounting looks good.
8) "Harry Potter and the Paternity Crisis" That one kid really doesn't look like Ron Weasely, when you stop and think about it. Hermione's not talking.
9) "Harry Potter and the Inland Revenue" -- Turns out Harry never paid taxes on the inheritance he received at age 11, and there's no way to magic yourself out of bureaucracy.
Anyone got other ideas as Harry goes from 17 to 36? In later years, one could go forward until, I suppose, we get to "Harry Potter and the Little Blue Pill."