Another option for the "crash across the finish line" challenge. Try Waluigi's Pinball Reversed. Time your banana throw right around or just before you exit the tunnel. It might seem like the banana fell too far away from the finish line, but the momentum is just enough to send you across the finish line.
Also there is a bizarre glitch where the challenge counts if you were to FAIL the "avoid obstacles" challenge, since the race would "finish" when you get wiped out and lose that last balloon, even if you didn't cross the finish line. So the game is only checking if you are in a "crash" state when the race has concluded, but not if it has concluded via finishing line. This might get patched out though.