"Way to go Roxas" is Hayner's default line, it's if you go all the way to 2k that he has a different line which is: "Wow Roxas, that's awesome!".
In the new playthrough I've started (and my first time ever in proud mode), I went to 2k because Roxas seems disappointed when he finds out how expensive watermelons are so I wanted him to be able to afford one and if I'd ever done it before I didn't recall if the characters acknowledge if he can so I was curious. Pence does. He'll say "We can even buy a watermelon with this!"
Strangely one thing I expected to change that DID NOT is that the total munny between the group still ends up being 5k regardless of how much you contribute.
Although I've done them all for the sake of the experience, I chose to accumulate just from the mail delivery and grandstanding.
The mail delivery is the quickest and the easiest and the grandstanding is the most fun, my record is 82 juggles.
These are also the only two I can get the max 50 from.
I didn't know you could keep going until the game would stop you?
At 2k Roxas will declare that "That should do it" and automatically head to the station.