The first time I tried this move I just did cheese rolls on starboard because I knew cheese rolls on starboard and I did shove-Its on port because I knew Shove-Its on port. This was not a surprise because of muscle memory; our friend when performing a move and our enemy when learning a new move.
I was pretty good at Cheese-Rolls and Shove-Its on their respective tacks so I knew I could learn this maneuver. I talked to Fredrick and then met with the infamous freestyle counsel in the Gorge, who dwell in hidden caves on Mount Adams and look like Yoda with board shorts. I was given ambiguous instructions in alien tongue then ordered to strip to my shorts and perform the ritualistic climb to the icy summit of Mt. Adams. This, like a lot of advice, did not help... unlike my advice of course, which does help... So I would like to believe... And continue developing this web site.
A few days later I saw my buddy Russ, an amazingly gifted and intelligent sailor, tossing a few Gutter-Flips at the Hatchery. So we had a little coaching session and I followed him around trying to be like RUSS. His Support was very helpful even though I never really figured the move out. For some reason, I dropped the move for a while.
Then one day at Upper Kanaha in Maui I spontaneously threw a Shove-It on starboard (the side I am trying to learn) and was certainly going to crash when my body, acting on it\s own volition... which it does a lot... threw my heels into the rotation and I was flipping over, pulling the sail along for the ride. Hey... that was a Gutter-Flip! Hey, that was a Gutter-Flip! Hours later I was "talking story" with friends about the new move I learned -- an indulgence every shameless windsurfer does once in a while much to their embarrassment.
So even though I have only made this move a couple times I am bold enough to say the difference between a Cheese-Roll and Gutter-Flip is during a Cheese-Roll you basically lay the sail on it's side with the clew back toward the tail of the board and continuously pull the sail thru the entire rotation whereas during a GF you lay the sail on its side but forward toward the nose and from that position you perform the rotation...feet 1st over your head... followed by pulling the sail over. Sure, there is a resemblance... Like a Back-Loop resembles a Push-Loop. But they are very different.