Are these sentences correct? (usage of conditional)

1) It would have been one of the hardest obstacles he ever had to overcome in his life
2) It would have been one of the hardest obstacles he would've ever had to overcome in his life
3) It would have been one of the hardest obstacles he had ever had to overcome in his life.

In my opinion, the 1st one seems incorrect, while the last two express different meanings (#2 meaning of all the obstacles he would've ever faced in his future, that one would've been the toughest; #3 meaning of all the obstacles he had ever faced in his past, that one would've been the toughest). But I want to make sure.

Thanks in advance!