I'd love to see what you've got for High Five. He is severely underrated in my opinion
(So sorry I took so long to answer this one!)
To be honest, High Five never stood out to me as a Skylander, as I never owned him, and only knew about him from the Trap Team 'THE COMPLETE COLLECTION' handbook. But after reading through his Wiki page, I can totally see why people would like him! His playstyle sounds super fun and surprisingly in depth for a Skylander! I definitely need to add him to my collection at some point.
Updated Origin:
High Five was always seen as a troublemaker growing up. He had troubles focusing, only ever barely passing his classes, and relying on his four older siblings to help him out.
High Five's true passion in life was racing. He wanted nothing more than to speed down the cloud paved roads and dodge the giant boulders that floated in between the course. He loved the thrill, the danger, the risk!
But of course, he was not allowed to do any of the racing, due to being far too young. High Five would often compete secretley in other, less prestigious races, under the moniker "Buzzerker", but he wasn't able to go into any big name leagues without risking getting recognized.
In his races, 'Buzzerker' had started to know the other little league racers quite well, building a bit of a rivalry with a few of them, namely a group of Troll racers by the name of "The Loose Screws". They raced with a rickety, hand built airship. High Five and them had been trading wins and losses for nearly the entire time that he had been racing, and he considered them to be good friends of his.
One day, he ended up letting slip that his family was the Royal High Flying Dragonflies. While they reacted positively at first, High Five ended up eavesdropping on them planning to steal the Trophy of Sparx from his family by manipulating him.
Betrayed and hurt, High Five refused to help them, and instead used his immsense speed and aerial skills to knock their ship out of the sky. While he was extremely hurt that what he thought were his friends had betrayed him over a magic trophy, his bravery was rewarded.
His family finally stopped babying him, learning that the "baby brother" they had always seen as a troublemaker was far more talented than anyone had given him credit for.
Additionally, Master Eon had heard of the race, and along with Bat Spin and Flip Wreck, High Five had been taken under the wing of the Skylanders and trained to be something more.
Other Stuff:
High Five has ADHD
He is known for being a bit self destructive, only ever wanting to go on dangerous missions and extreme race courses. Even speed demons like Roller Brawl think he might take things a bit too far sometimes.
High Five has extreme, debilitating claustrophobia. He gets uncomfortable in normal sized rooms, and when they get smaller, it goes into panic attack levels.
Despite initially seeming extremely different from each other, High Five is best friends with the skylanders he was trained with at the Academy: Bat Spin and Flip Wreck. They initially bonded over the fact that they all were recruited by defending their families, but they soon found that they shared a ton of common interests.
High Five's expertise at air travel and flight made him a prime candidate to receive a Supercharger when the time came for them to be initiated, but High Five refused, as he much preferred flying over being cooped up in a cockpit. The role instead ended up going to Stealth Elf, and her appropriately named "Stealth Stinger".
That's what I could come up with for High Five. Do you like it? I'm always down for feedback, as long as it's polite ^^
I named his racing alter ego after his In Development name (Buzzerker). His somewhat self destructive nature comes from how much his designer went back and forth on his self damage and poison mechanics, thinking that it would make people like him less. The only other thing I'd want to specify is that I made him friends with Bat Spin and Flip Wreck because those three were the winners of the Frito-Lay designing competition, so it seemed natural that all three of them should stick together.
