I think that style wise Machida was still a tough match up for Hendo and I still think he would have won that fight. I recall Dan fighting Rich Franklin around that time, and even though he won it was a very close fight. With that said, I think Machida would have the capability to do better then Rich. Machida was in a good grove at that time, he beat a few top LHW's around 08/09.
Regarding Machida at MW?? Yah…if he would have made the move earlier I think he would have done very well and been champ for a long time. Anderson at LHW?? Who knows…..he killed everyone but never really fought a top fighter at the time aside from Forrest. I still think Anderson would have the potential to be champ at LHW, the division was Rampage, Couture, Rashad, Shogun, Forrrest, Bader, Chuck at the time.
Win/Lose always in support of my fav fighters
Minowa SHW goat