TAR 31 Rowing race detour task. Almost everyone couldn't even figure how to balance the thin boat perfectly, and it took 4 attempts and a genius strategy from Colin and Christie to complete the task
I thought that TAR 30 final task was also brutal too. I don't remember how many attempt the other team had to do to complete the task, but it took 10 attempts, and roughly 2 hours from Jess to complete the task.
The basket delivery task on TAR 29 2nd Vietnam leg RB is definitely on my list too. The climate + how heavy the baskets are, especially when you have to deliver it by bike, took Floyd the hardest way. Other teams struggled heavily too. I actually didn't expect could be so brutal as switchback, remembered that this task was actually one of the funniest moment on TAR 3 with the same task (although it was ARI)
TAR 24 Cocktail mixing detour task. Man that was gritting. I remember this was (and still) my favorite task ever on TAR. Many teams pretty much struggled to do this particular task, and Margie and Luke were the heaviest victim of all, especially when they had to do the task because the other easier detour task required hearing. altho they weren't in the last place eventually, this was really painful to watch. I was kinda impressive that Jet & Cord took merely 3-4 attempts to finish the task.