I love Riley, and while I do think he acted like a jerk in the end, I agree that he could have been the long haul guy under the right circumstances. I think their relationship was sabotaged by bad timing (Joyce's illness and death would have tested any relationship) and failings on both their parts, but there's a lot of coulda woulda shoulda in that ship.

The seeds of Willow's self destruction are well and truly planted as early as season 1.

Yes! This is what I was trying to say with "Transparent," all those years ago. Her need for control, her willingness to overlook the means as long as the ends score a win for her side, a distinctly fungible moral attitude...it was always there.