A car pulls into the parking lot of your apartment complex with rap music blaring, and with the driver rapping and singing along. Three people exit the car. Do you really think it's a good idea, in such a context, to tell your friend -- out loud and within the hearing range of these people -- that the driver's singing sounded like a song that Elmo (from Sesame Street) had rapped? Will this really be the start of something good?! Especially when, in response to the driver's "question" as to whether you're trying to be funny, you make a point of calling him "boy"? Not good. Not good at all.
It actually sounds like the victim in this case was somewhat of the aggressor. That said, when the defendant and his friends (after substantial additional confrontation) got back into their car, and the victim leaned into the window of this vehicle, at which point the defendant produced a gun, I agree that this upped the ante, and that the roles were suddenly reversed.
I have very little relevant personal experience on this point, but even my limited knowledge of the mean streets inclines me to agree with Justice Nicholoson's conclusion that defendant was indeed guilty of making a criminal threat. Sure, the only thing defendant said at the relevant time was: "Is there a problem?," and in a wide variety of other contexts, I'm sure that wouldn't be a threat. But when you add "bitch" to the end of that sentence -- turning the statement into "Is there a fucking problem, bitch?" -- and when you repeat it by saying "Is there a fucking problem, bitch?", I think we know what you're saying. Especially if, when you're saying it, you and your two friends are holding and displaying handguns. I get the message. It's a threat.