Doting Parent: Becoming poor made him closer to his family, and comes to realizes how much he loves them over Martial Arts. He even asks Master Hung in the second film "Which is more important; our battle, or having dinner with your wife and children?"
Real Men Wear Pink: Granted he is garbed in black 99% of the duration of both films and never literally wears pink, but it's mentioned a few times that Wing Chun was invented by a woman. The name itself means something like "eternal springtime" or "spring chant" depending on who you ask.
Riches To Rags: He started out a rich man, then was forced to live in abject poverty when the Japanese occupied Fo-Shan.
Ip Man's wife, played by Lynn Hung. She disapproves of her husband always fighting and wants him to spend more time with his family. She has two sons: Ip Chun, played by Li Chak, and Ip Ching, born at the end of the second film.
A businessman who owns a cotton mill being plagued by Jin's bandits. His family flees to Hong Kong with Ip Man's family but he is shot in the head by a Japanese soldier. This causes him to forget his family and friends, thinking that everyone he sees is Japanese.
Easy Amnesia: He is cured after hearing Ip Man beat Twister on the radio.
Blood Knight - Though more to prove his name than out of pure bloodlust, mind.
Defeat Means Friendship: Not in the first movie, mind you. But having the arrogance knocked out of him allowed him to find love and build a happy family by the second film, something he has come to thank Ip Man for.
Doting Parent: Having an adorable little girl is yet another incentive to turn away from a life of violence.
Easily Forgiven: He had been involved in Ip's life three times in the first movie: first he challenged him to a duel and accidentally smashed up his house (and attacked Ip with a sword), then he had become a bandit and tried to beat and rob the factory Ip was helping at. Finally, he gave Ip's location to the Japanese who were hunting him. Yet when he reappears in the sequel, he's greeted as an old friend.
Handwraps of Awesome: in the beginning of the first movie, he has his right hand wrapped up. Appropriately, his style is much more brutal and powerful than anyone he faces... until he reaches Ip Man.
Defeat Means Friendship: Doubly subverted. At first he rejects Ip's offer to be the man's student and came back with friends for another round. When he's conclusively shown the error of his ways, though, he gladly accepts the tutelage.
A Hung Ga master who started out as his enemy but later became his friend. Played by Sammo Hung.
Acrofatic: A rather mild one but nonetheless he looked out of shape and yet managed to do acrobatic things to keep up with Ip.
A Father to His Men: Master Hung's students are largely orphaned delinquents who are forced to turn to criminality to stay alive; by giving them a home along with his teachings, he gave them a second chance at life.
Necessary Evil: He is something of a Jerkass and Opposing Sports Team to Ip Man early on, but it quickly becomes apparent that his rules, fees, and attitude are necessary for the martial arts schools to remain afloat under British rule.
For the Evulz: Publicly humiliates Chinese Martial arts and gleefully beats a sick and elderly Chinese Warrior to death because the British Government has his back covered; with a huge knowing smile on his face
Villain with Good Publicity: Due to his connections, the British audience seem to think of him as just a popular, skilled boxer. Given the way they cheer for Ip Man's speech at the end this may no longer be the case.
A Chinese police officer in Hong Kong who ensures that the martial arts clubs comply with the British police. Played by Kent Cheng.