With regards to sculpt, it's interesting to see the two together, unpainted. You really get an appreciation of the strengths (and weaknesses) of the two approaches.
I think the SS head with a repaint, with the HT remaining would be the ultimate Obi Wan. Not sure bout the inner robe though, it looks like a see through material on the HT one. Looks like something Rey or Padme would wear instead of Obi Wan