Has dyscalculia. His focus shift from projects, often leaving most unfinished. Respects Hero to a very high degree, modeling himself after him. Legend states that he has a unique ability to connect with the public, compared to the rest of his team.
As a Tinker, Chris has the ability to understand and invent things well beyond the current level of technology. He originally believed that he specializes in advanced guns though later discoveries showed that his specialty is actually multi-utility devices.
Thought he had an affinity for laser pistols before he realized what his specialization truly was.
Kid Win was diagnosed with ADD and dyscalculia before he gained his powers. Although he resisted the ADD diagnosis, he couldn't deny the dyscalculia. He became even more distractible after gaining his power.
A year and a half before the Sentinel arc, he was in a similar position to where Chariot was when they met - scavenging for resources, fiercely protective of what tech he could manage to create.
With great difficulty, he managed to create a hoverboard, driven by the thought of how awesome it would be to fly.
At some point, he was prescribed medication for his ADD by the PRT's doctor. During the two weeks he was on it, he found himself vastly more effective, and constructed a powerful Alternator Cannon. He was forced to stop because of adverse side-effects. He didn't have a chance to run it past the PRT military and science teams.
Deployed the Alternator Cannon, meant for an A-level threat, against a group of super-villains to stop them robbing a bank. He got into trouble because it hadn't been cleared; he underwent a disciplinary review and Piggot confiscated the power source.
↑Kid Win – A tinker serving in the Brockton Bay Wards, favors laser weapons and a flying skateboard, with red and gold body armor. - Cast (Spoiler Free)
↑Chris Kid Win Tinker specializing in alternate settings or uses. Struggles to build more focused devices. Wards Tinker 4 - Parahuman List, bolded edit by Wildbow
↑ 5.05.1Kid Win, Chris – A ‘tinker’, Kid WIN has the ability to invent things well beyond current levels of technology. After a long period spent struggling to find his niche, he discovered his powers didn’t center around laser guns as he’d thought, but around modular equipment. Initially modeling his outfit and his weaponry on Hero, the first tinker, Kid Win is in the midst of finding his identity. Wears a costume of red and gold, with red lenses and a characteristic red glow where he uses antigravity gear. As a tinker, his costume and gear change on a regular basis. - Cast (In Depth)
↑ It’s not customary for tinkers to design things for teammates. If they do, it’s on a relatively small scale, simple. Kid Win making Gallant’s armor, for example. - Excerpt from Drone 23.5
↑He was dumb, easily distracted, prone to leaving his projects unfinished, and it was moments like this that this knowledge hit him particularly hard. His dad had made him get tested, and the doctors had labeled him with ADD and dyscalculia. He held to the opinion that the ADD diagnosis was way overused – he liked to think that he was just a daydreamer, prone to getting lost in his thoughts.
The dyscalculia was something concrete that he couldn’t deny or explain away. He couldn’t keep numbers in his head, couldn’t make the most basic intuitive leaps or connections with them.
All of that had been before he got his powers. Nothing had changed, except that now he could visualize something, instinctively know how he could put it together. His disability or disabilities put him a step behind the rest. His daydreaming was worse, because his thoughts were so damn interesting, now. He couldn’t take reliable measurements without using computers to do it. Couldn’t finish half his projects without feeling compelled to move on to something else. -
Excerpt from Sentinel 9.4
Kid Win paused. This is like looking into a mirror to a year and a half ago. “Look, I can see your TV, your toaster. Chances are you’ve gone to the Trainyard or a scrapyard to find some stuff. Old batteries, car parts, chains, good metal, whatever.”
“I get it. Been there. You’re hungry to use your power, but more than any other kind of cape, you’re facing a hurdle in terms of the entry-level resources you need. This is where the team would support you. You get funding, a lot of funding, to put your stuff together.” - Excerpt from Sentinel 9.4
↑ 9.09.1There were exceptions. He’d finished bigger projects. His hoverboard, driven by the idea of how awesome it would be to fly. Even then, it had been a chore. Monumentally stupid of him to dismantle it. The idea and motivation driving the action had been good: he was graduating the Wards in a little while, he’d be expected to change his name and adjust his methods, because an adult calling himself Kid Win was lame. He’d had an idea about a harness with a floating array of turrets that could fire different munitions depending on what gun he holstered in the main slot. Self adjusting and adaptive the way his Alternator Cannon was. Except he’d gotten frustrated at a snag in the testing, put it down to take a break and hadn’t picked it up again in six days. His hoverboard had effectively been destroyed for no reason, when it might have made the difference in getting the Travelers into custody. - Excerpt from Sentinel 9.4
↑ 10.010.1His Alternator Cannon was the real gem. It had been the result of a medication the PRT’s doctor had prescribed, which he’d been forced to stop after two weeks when he began to get increasingly dizzy, anxious and nauseous. While he’d been taking the pills, he’d been focused, had a glimpse, maybe, of what he could do if it weren’t for his distractibility and daydreaming. When Piggy had spoken of destroying the thing, the mere thought had been crushing. Then Leviathan had destroyed it for real, maybe the only truly brilliant thing he’d be able to make. He harbored fears it might even the only brilliant thing he’d ever be able to make. - Excerpt from Sentinel 9.4