Pump and hold R2 on the opposite quarter pipe from the actual gap, where the two arrows are located. You should have enough air coming down. Use that speed and air with an angle to jump the gap. Use the R2 trick on the tranny of the gap.

To do the Hip to Hip Transfer easily, skate to the corner that you first have to launch from for the transfer. Set the Session Marker and push once towards the middle of the opening of the marked corner. Do not go too fast to avoid bailing. Get off your board when you get to that corner opening. Make you do not touch where the transfer begins. Walk across the pool to where you are supposed to land the transfer. Jump once while off your board, then jump one again, but this time get on your skateboard in mid air. Land on the bottom wall of where you are supposed to land the transfer. If done correctly, the transfer requirement should now be highlighted on the list. Grind the siding to complete the challenge.