doobie, edge a little harder toward the wake, a more progressive edge though, should be way easier then. Also, if you're having trouble landing, try some small wake jumps from the inside of the wake to the outside on your heelside.
If you can, get an pylon attatched somehow, it will make it easier But you should still be able to do it without it. Can you wake to wake at 55ft with your wakeboard? if so, can probably do it on skate.
hope that helps