i think it stems from the fact he can do every single trick. he can do it on every single setup, its just a matter of how much he is struggling with it on certain day. so one day a sw 360 flip takes him 1 try, the next it takes him 3 or 4. if he wasnt so picky then even on the bad board, i think he would get used to it and eventually get it to the point he can do it every try.
the real madness is when one setup works better for certain tricks, but then worse on others. i noticed he was like "oh i really like smith grinds on ventures" it is kind of an oddly specific trick to call out. theres never gonna be any 1 board that does everything perfectly. when you add length to the wb, to me it feels harder to bring around on 3 flips, but i find increased stability and control when doing grinds or skating transition. will chnage the way you manual too. then you bring in the bolt position, concave, and steepness of kicks. i feel like that stuff more comes down to preference but again there is a similar trade off and the timing will change.