CHILDHOOD - 1861-1872 | Benji has a generally normal, if lonely childhood - the Woodcrofts are more or less the only people who live in Hogsmeade full time, and they own and run the inn, the Three Broomsticks.
1873 | Benji goes to Hogwarts and is sorted into Gryffindor.
1875 | Benji decides he wants to be an auror, if he does not want to run the Three Broomsticks, and becomes peripherally aware that his father goes to London to gamble.
1877 | Benji comes back from Hogwarts to discover that his father has gambled away the Three Broomsticks. Honestly what the fuck.
1878 | Benji acquires several OWLs, but the Woodcrofts don't have the money to continue. In that awkward phase where he cannot perform magic legally, he takes to working in the Hog's Head rather than work for the man who won his father's business. His other hobby is fighting with his father.
1880 | After turning 17 at the end of 1879, Benji becomes an intern in the Department of Magical Law Enforcement - he had always wanted to be an auror, and this is almost close.
1882 | Benji becomes a regular MLE employee.
1884 | After his father nearly gambles away the house, Benji gets in a blowout fight with him and moves to a different house in the Slums with some friends; he also becomes a police constable. It's not quite auror, but it's at least better than being a typical DMLE employee - and he does not have to be near the real aurors, or the Three Broomsticks. Benji and dad make a big show of forgiving each other around Christmas, although things remain tense. Benji is an extremely patient constable, especially with those who gamble; no one who gets in trouble at the casino can have done anything nearly as drastic as his father has.
1889 | Around the end of the year, Benji and his father get in yet another fight over the Three Broomsticks; they have not spoken since. He is not on speaking terms with Abigail, either, but at least Ellie still likes him.