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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
Special Agent Oso
Oso really is "oh so special".
One of his parents is running a full-on special agency (undercover work, assassinations, the whole James Bond package), and uses company resources to teach their mentally handicapped son basic concepts.

Oso and his other animal friends are really a spy agency's series of stuffed animal androids who escaped with a large chunk of the agency's tech and resources and are now secretly performing their own plans .
Multiple times both Oso and the kid he's helping state that Oso is just a stuffed bear, however, the fact that he can move suggests that he must be some sort of robot. This also applies to his other animal friends at the spy agency, they are all stuffed animal androids. However, Oso is defective, but rather than reprogramming him, Wolfe and the others are simply retraining him by having him help little kids. Meanwhile, the properly working androids are busy plotting their real plans involving real spy technology, while they keep the defective Oso in the dark.

Oso's agency was created as a decoy for an actual intelligence group.
No one's going to suspect an agency that helps kids stand in line for petting zoos and trains for ridiculously easy scenarios (Get the computer chip on the podium only using this stepstool, enter the ice base by walking up to the front gate and saying the password, etc.) of actual espionage. Oso hasn't been told in the event he's captured and interrogated. Or, Oso has been told and is playing us all for fools.

The show takes place in an Alternate Universe where war is abolished and all the countries get along.
All the spy agencies now have nothing to do, and rather than lay them off, the government retrained them to help little kids, with training missions to make them still feel like spies instead of overpaid babysitters.

Oso exists in the same universe as Monsters Inc
They've somehow managed to harvest happiness, which is why they go to such extreme measures to keep kids happy.

The agency Oso works for is a U.S. Government Agency, and is the primary reason America has a rapidly rising $14 Trillion+ Debt.
So Oso is constantly being trained using very high tech equipment, in varied locations around the world (including deep in the oceans, in the Arctic, and on the moon), and requires rapid transportation to arrive at his assignments, including sentient bullet trains, helicopters, and the like. Then his mission consists of helping a child eat spaghetti without spilling it, or teaching another child to fold the laundry. The only logical conclusion is that for every child Oso gives a seven minute lesson on doing some ordinary task, it costs U.S. taxpayers approximately $40 billion.

Mr. Dos is the Big Bad all along.
One thing I know is that all the kids around the world know how to do those simple tasks. It's just maybe Mr. Dos has hypnotized them into forgetting how to do those things. This is his plot to distract Oso from his training exercise as he knows he really is stupid to do it. His henchwoman, Paw Pilot becomes sympathetic to Oso that she has given him tips on the special steps, and gives him enough time to finish the assignments.
Space Ghost Coast to CoastWMG/Western Animation (Series)The Spectacular Spider-Man

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