Adam, ultimately it's practice that will help you with your ollies and wake jumps. I learned how to do all of the basics (wake jumps, shoves, ollies, etc) on a flat deck, and the first kickflips were done on flats (in fact, some of the popular tricks nowadays were done on cutdown wakeboards). Needless to say, there isn't a magical board that will make any of these things easier--it's all about practice.
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