A bit of added context here.
Orosco retired from parkour/free-running at some point during this period, I'm going to say mid-2010s (I know he competed in Vancouver in 2019 but this was a one-off). And has been mostly focussed on CrossFit since then. He also retired from ANW after ANW6 which would've been 2014, and his last ever Ninja appearance was X-Warrior China in 2015. So I'm factoring these in to my predictions given that sports like CrossFit aren't as conducive to doing well on Sasuke compared to parkour.
27 - Either UCH or Wall Lift (he failed the UCH in Boot Camp for ANW3, and he was always kind of slow on Stage 2 so may fall foul to reduced time limit)
28 - Swap Salmon Ladder
29 - Backstream or Passing Wall
30 - Wall Lift
31 - Crazy Cliffhanger
32 - Flying Bar if high 90s, TIE Fighter or wall if low 90s, otherwise still Flying Bar
33 - Fish Bone or Stage 2 timeout
34 - Fish Bone or Stage 2 timeout
35 - Dragon Glider
36 - Dragon Glider or Stage 2 timeout
37 - Sidewinder
38 - Reverse Conveyer
39 - Warped Wall if he ran in the rain, otherwise Stage 2 timeout or max Swing Edge
40 - Stage 2 timeout or max Swing Edge
My predictions are based on his real life career/training regime changes, and assuming a bit of Sasuke-specific training but obviously no access to all of the replicas in Japan and the fact he's not reappeared on ANW. By the time 40 rolled around, he would've been out of the Ninja and parkour game for 7 years, and would also be pushing 40, hence why he declines after 31-32 for me. A lot of the Stage 2 timeouts are based on the fact that he was never that quick on the stage, and his weight would work against him on the Salmon Ladder and Spider Walk.