The fact that he calls himself a conservative and yet feels left behind by 'his' party that has run off the rails pandering to a few key demographics is part of the drama.
The problem is that it's really poorly presented on the show because, based off of what we've seen, Will is not really a conservative. On almost every issue that the show has addressed, from gay marriage to gun control, from social security to free-market economics, Will has not expressed traditional conservative points of view. The sole conservative value he was shown to hold is that he's pro-life, and that was a single line thrown out there in an episode about an entirely different subject. In the same episode he revealed that the reason he is a Republican is that he grew up in a rural area where everyone is a Republican and that's all he knew. I hate the overuse of the RINO label as much as anyone, but Will really does come across as a Republican in name only.
Let's be honest here, the reason why Will is a Republican is that Aaron Sorkin wanted to go after the Tea Party and he felt that having the main character be a Republican would act as a shield from the potential criticism of the show's liberal leanings. But he did a really poor job of portraying Will as a conservative, it's one of the leading criticisms of the show, and it's a good sign that Sorkin is trying to address that in season 2.
I think the show hasn't touched on a number of issues. The first, is the role of government in our lives. The second is the role of business in our lives. He hasn't gone into debates about "truther-ism" or touched Obamacare.
The show has talked about the TEA Party, and if they are really true conservatives. And while it may have not gotten much media coverage, there is a struggle within the Republican ranks over the role of the TEA Party. That
was touched on.
It's common sense to ask "why weren't the rigs inspected" in the first episode. And if he's not aligned with the TEA Party, then he wouldn't be for ending worker's rights.
As for Mackenzie, I think the beginning of the show shows her to be the idealist. She is the one who is pushing Will. And as the series progresses, she becomes more unraveled because of her feelings for Will. That's a mistake and why I want them to resolve this issue fast in Season 2. It's robbing us from seeing her as a strong female character. At first, she was. Until she sent that email. She's the one who is in charge.