I think you overestimate his ability especially with the cliffhanger. He's never beaten a version of it in official competition, his weight works too much against him. On modern ANW he has really struggled.
28: Spin Bridge most likely given he's failed similar obstacle too it on ANW. Maybe he could clear if he was lucky. In that case either a swap salmon ladder dq or crazy cliffhanger jump.
29: Swap Salmon ladder dq, backstream or passing wall time out.
30: Swap Salmon ladder dq, wall lift or crazy cliffhanger jump.
31: Warped Wall timeout most likely given it was raised and the tackle. Maybe his height could help him in which case, probably a lumberjack fail. Best case scenario for him would be the crazy cliffhanger jump.
32: I'd say TIE fighter, Double Pendulum dismount, Warped Wall or Lumberjack Climb. There is a decent chance he would be running in the rain before Drew's run. If he got really lucky I think he could clear and stage 2 wouldn't be an issue so on stage 3 he'd either fail the flying bar, sidewinder R or in the best case the first jump of the UCCH.
33: He could fail at the same spots as 33 including the fishbone as he has struggled with balance obstacles. On stage 2, I think the final combo would drain him out and he'd time out at the wall. In the best case though the glitched flying bar, I really wonder besides Drew who else could have beaten it.
34: At this point the stagnant stage 1 (and stage 2) would be less of an issue for him but anything could happen. On stage 3, this could possibly be his first chance to beat a crazy jump but only the first one. So either the first jump or the second jump would be his best.
35: Agree with Dragon Glider as he has struggled on its version in ANW.
36: Dragon Glider probably again. Best case scenario the second jump of the UCCH.
37: Dragon Glider again, maybe similar to Darvish where fog screwed him over. I do think however he could beat the stopped cliffhanger dimension here but he would have to be really f***ing lucky and would have to train relentlessly prior. On the VLT, although it did have thicker ledges, David is still one of the heavier competitors and would have never attempted it before, him beating it may be possible but it would be 1 in a million. So in this case for 37, Dragon Glider, Cliffhanger Dimension, VLT and in a miracle scenario the salmon ladder Jugo Dan.
38: Agree with Wall lifting.
39: Warped Wall most likely. If he has good luck then probably the swing edge.
40: Agree with cliff dimension second ledge if he keeps up with his training.