Okay, time to get creative and actually create some lore. Only had time to do the five longest-tenured villagers from Wahu (it's after midnight for me as of posting this), but I'll definitely do the other five and may also do Parkwood at a later date.
Intentionally avoiding sensitive and debatable topics because this is an E rated game soz 
Patty
It was tough for Patty growing up in the countryside. There was no one around for miles, and she became quite a lonely cow. The few friends she had all abandoned her because she would often build up steam quickly whenever she was upset, and there was always destruction involved due to her size and nature.
Patty knew that her occasional erratic behavior was unacceptable, and wanted to start fresh elsewhere, preferably an area where she could make many new friends. On a random visit to the local travel agency, desperate to find some new neighbors in a new town, she came across a pamphlet for Wahu, advertised as "the place to make lifelong memories". Immediately intrigued, she immediately packed her bags and booked the next flight to the quaint island.
Even though it took some time to adjust to her new island life, she eventually grew to like the new scenery, and made a pact to remain a permanent resident on Wahu. Now that she's been there for a while, the other villagers sort of look up to her as a role model, though sometimes they still get intimidated by her presence in a few tense situations that arise because of her past history, but for Patty, her behavior today is miles better than it was back when she lived in "Nowhereland". She loves being the popular cow in town, and likes to spread her positivity in any way she can.
Bob
Bob never quite grew out of his childhood phase. Ever since the "crayon" incident long ago, his thinking functionality hasn't really improved a whole lot. He became hyper-focused on video games, but only those that are considered "edutainment" to many. He has yet to learn how to speak at a slower pace, as his quick speech patterns tend to cause him to start talking gibberish and make less sense to others.
One day, while living in his Grandma's house, Bob wanted to ride in a plane, just to see what it was like to reach the clouds and "taste" them as they reminded him of cotton candy. Grandma was a bit hesitant, but agreed that she wanted to go on a vacation to somewhere. On the flight, Bob started licking the window, but realized he couldn't make his tongue go past the glass. It got to the point where Bob nearly opened the emergency escape door and caused a scene on the plane. DAL officials (and Grandma) realized that he was being a danger to everyone riding the plane, and agreed to dump him off at Wahu.
Once there, he met the island representative, Trevor, and they became fast friends because they found each other incredibly funny. Bob decided to set roots then and there, and his older relatives all agree that he needed the taste of adulthood. Only time will tell if he will start showing some maturity...
Mallary
Oh, where to start with Mallary. Let's just say that she's more of the "city-dweller" kind, and wanted to remain like that when she previously worked as the secretary for a famous TV lawyer. However, there were various allegations that said TV lawyer was bribing city officials, which Mallary eventually heard about through social media, and wanted nothing to do with it. After every TV network in the area wanted to interview her about her boss' shady deals, she had enough and wanted to get away from this swarming media storm.
Mallary went to the International Airport and told the attendant behind the counter that she wanted to get as far away from the city as she could, no questions asked. Since Mallary kept a neutral profile throughout her career and prevented her boss' habits from spreading to her, she was able to get away and not look back. The attendant booked a flight for Wahu, since it was a tiny remote island with some friendly folk that got along with each other well. Mallary called her boss, told him "good luck" with his situation, and was on her way to a better life.
Once in Wahu, Mallary immediately felt like she was home all along after finding a property that resembled hers back in the city. Her neighbor, Dotty, sometimes gets on her nerves due to her rather bubbly personality, but at least Dotty doesn't spread rumors like certain villagers back in the city that Mallary would like to keep unnamed. She grew accustomed to island life rather well, and doesn't look back.
Cherry
Cherry was one of the "cool kids" back in her hometown. Having had lots of friends and having connections to some rather famous rock musicians back in school, Cherry was the one the other kids wanted to be.
However, after graduating school, Cherry realized that all the fame she had would go to her head rather quickly if she continued to live the life she had clamored about for so long, and could eventually put herself in danger. She had to come up with a plan to somehow lower her social profile, and an idea struck her after hearing a suggestion from one of her old rock buddies: "If you want to get away from the big crowds, you've got to lay low. Find a place you can dig, and start living the life you want to live. Only trust yourself; don't let others influence your decisions."
Cherry called up one of her musician friends, and they suggested that she seek a permanent vacation on Wahu. They said that there's not many villagers to worry about, and everyone likes each other equally, so nobody can be the super popular one. Besides, no one else can move there once the island fills up, and she could lay low there as long as she wanted to. Interested, Cherry flew to Wahu, signed some housing contracts, and was on her way to living a more private life. Today, she still maintains her "popular kid" mentality, but only with the island residents and never with the outside world, and she couldn't be happier with her decision.
Tom
Tom had been retired from the Junior Bantamweight League for a long time, having won several championships, and at one point being named the Junior Bantamweight king by several magazines. After his retirement, Tom started to become bored with everyday life, and missed the glory days of when he was a sports superstar.
One day, Tom decided that he wanted to go back into the ring one last time and prove to everyone that he can still take on anyone he faces. His first opponent, Lucha, was just coming off a massive victory against reigning champion Stinky, and wanted to prove to everyone that he is the new king of the ring. In the first round, Tom couldn't even land a punch, and faceplanted onto the floor after losing his balance. In the second round, he regained his composure, and started to take on Lucha for real. Unfortunately for Tom, due to his age, he got tired rather quick, and Lucha won the match after knocking Tom stone cold.
Incredibly embarrassed by his defeat, Tom retired again and moved to Wahu to remind him less of his old days. Even though he may act a bit cranky towards the other islanders, he is still the most respected one of all due to his wise and mature way of handling situations, and has completely put his fighting career in the rear view mirror.
sometimes the game just naturally works in your favour heh
and the whole dream proposal... meanie
whatever could this mean. me too!!!! sometimes i can get too excited and talk way too fast, way quicker than my mouth can keep up so i'll have to take a breather then start the sentence over but sloooowly this time. THEY JUST DUMPED HIM....poor baby
