Make sure you play on Chrome if you want a chance at the Bankrupted Joe the Player medal. I'd done most everything else in Firefox but that mini-game is bugged in Firefox and makes you lose no matter even if you chose the correct cup. I really hate when people put in browser-specific things in games (or fail to test it works the same on the major browsers). Someone who had the medal told me he'd done it in Chrome and was wondering why so few people had that medal -- well there you go it must be done in Chrome browser. I believe everything *except* that can be done in Firefox.
If you want a chance at Beat Speed Racoon practice up on King of the Slope (another game by jacklehamster) as it's basically the exact same game except you can't beat up the other skiiers and in fact if you crash into them it'll hurt you and not them.
Most of the game is twitch-perfect controls and pixel perfection required in some areas. It's a quite awkward control scheme. Space to jump, space to wall-jump, space to change direction in mid-air (to position yourself going the opposite way once you land). Remember that last one as it's necessary to get at least one of the penguins.
A good question to ask is why is Darwin Gator friends with that annoying penguin? He should probably leave the penguin near a volcano and tell him there's fish inside, then just skateboard away.