His mom is starting him on a healthy diet of retro platformers and old-school
RP Gs.
As for pony shadows, I think the most difficult part of them would be differentiating them from one another. Many of the ponies issues seem to come down to worrying aout their value and wether they're good enough to have friends, it seems. Twilight seems terribly worried that she doesn't live up to Celestia's standards, Pinkie is worried that ponies will tire of her parties and, by proxy, her, Dash seems to have the idea that her worth is tied to being the best... if we follow the comic then Rarity also seems to worry she's just buying her friends' attention.
Fluttershy and Applejack, at least, seem to be unique. Fluttershy has her repressed anger issues to deal with, and AJ seems alarmingly close to nihilism at times - especially the comment from her focus comic about wondering just who IS in charge of making sure everything turns out fine.
It might not be so hard to break the chunk of 'I'm not good enough' apart, though. Pinkie's fear is foundedi n the belief that nopony really knows her on a personal level(Shed actually make a decent protagonist for a Persona crossover in that her fear is founded in personae themselves). Twilight's fear can be said to stem from the fact that she essentially got where she is
by accident, and doesn't know if she can pull it off on purpose. Dash's problems seem to be at their worst when she's in danger of being left alone, which speaks to abandonment issue(Which would explain her need for attention being far more present and real than Pinkie's or even Rarity's), and Rarity herself, well... she seems to be fully aware of her faults, and so is probably worried that ponies just think she's a
bitch.