I watched Dr. Wills first season and here are my thoughts:
He is kind of a strange guy. I cant tell if hes a sociopath or what and his taste in women is horrible. I was expecting to like him personally, but I was mostly indifferent.
There has been some debate about how Derrick compares to Will, but its sort of apples and oranges. The game has evolved, for better or for worse. For example, people in season 2 were a lot more trusting than they are today, there was no veto, no jury house, and other key differences.
Will was awesome because he told people he was lying to them and that openness essentially got him through the game. Derrick actually controlled the nominations and votes a lot. Will didnt really do any of that but he also didnt have someone like Cody to win comps for him. To Derricks credit, Cody took Derrick to the finals because of their alliance, whereas Nicole took Will to the finals because she thought it gave her a better chance to win.
Will put a huge target on his back and then weathered the storm, which worked out brilliantly, because he kept on getting a pass while the house was voting out more likable people. Id say Will and Derrick are pretty even. Both of them were great psychological players. FWIW, even Boogie said Nicole played the best game in Season 2 but then he voted for Will.
I am now watching BB All-Stars, and Will is the only winner, so Im excited to see how he pulls it off this time. This is probably where his legend is really built.