Yeah, he is haha!! I wonder if that reaction is specific to the character who finishes in second place or if it's meant to expose a connection between Yoshi and Catherine.
Nope. I play on a console and I did this twice. First with Mario and then with Yoshi (the run you see here). *Correction - I made it to 999 with Mario in 39 turns but lost 40 points on the very last one and ended up at 959.
When you enter Challenge Mode, the game lists a description of each goal you need to complete in order to make your character a Superstar. Just take it one step at a time with one character.
I'm currently unable to make a tutorial video for you and I don't know of any that are on RU-vid. You need to read the manual to learn the controls and how to perform the moves. After that, you can go back to GameFAQs for help.