The quirky controls will be the most difficult thing to overcome. You can Start the game and stay in the training area for a bit of an easier time but I found this easiest to complete by kicking off and using the to steer continue directly up which is more your upper left, and take the first street on the left continue down and up into the alcove to purchase the hotboard then head back the way you came and take the first street heading upwards this will bring you to the downhill ramp. I found that jumping to cut corners actually makes this harder and followed the concepts of this video.
Anyone have a suggestion for the easiest event to get a Gold in for someone that's NOT really great at skateboarding games? LOL. I'm thinking the downhill race one seems pretty straightforward, I just keep screwing up on the landings.