Anyone who saw Mathew in Amistad, dazed and confused, frailty and a time to kill knew this guy could act, I always used to wtf in the 2000s when I read his upcoming projects were all rom coms, but in hindsight and reading his quote about pacing yourself in life it makes sense.
He used his thirties to make the easy money with well paying romantic comedies that he could sail through ,using his looks to cash in on, then approaching his mid forties, when he is financially secure and had his youthful fun, where typically make stars can't bank so much on their looks anymore, he makes the switch up that he always, and anyone that had seen his early work, knew he could do.
As for the show, it's very difficult to predict how it's going to end, though I agree Woody doesn't seem to have shown all his cards yet.