Why all the Pipsqueak hate?

It was more the "Here's a pony that everyone knows but is shown with little-to-no explanation. Have fun." sort of mentality behind him.

Well, he just moved from Trottingham, apparently.

I guess I really didn't mind it. It's a lighthearted show, after all.

It's implied that Twilight is tied in with the Ponyville school (she's been seen working with Cherilee at times, and she's also the librarian), so perhaps that's how Twilight knew him.

Or Pinkie threw him a welcome party as usual.

Or I'm overthinking a kids show again.