IMO, I would try the backroll first. You don't change much from a normal wake jump vs a trip flip. I was like you, I will do front flips off of anything, never spun backwards (on trampoline, diving board, ect.) and still haven't and won't. But I will on a wakeboard. weird, I know. For my first backroll, we slowed the boat down to 19-20mph, as slow as we could and still keep a clean wake. I tried one wake HS backroll. Of course I didn't make it but it got me over the fear and actually supprised me at how natural it was and the crash was nothing. After that I started trying full on backrolls. Once you try it, you'll get over that fear real quick. Just go for it man.
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