When you consider what the FO's philosophy was, that the rotation was not supposed to be lights out, but only decent enough to give the offense a chance to bail them out, I don't think the question marks were as huge as it seems. There was no reason to expect that Porcello, Miley, and Kelly couldn't at least repeat last year's seasons. There were question marks regarding Buchholz and Masterson. but there were also youngsters to step up in case Masterson didn't work out. The problem wasn't so much Masterson not working out as it was Porcello, Miley, and Kelly not performing up to expectations, not to mention our offense being MIA in May.
As far as the $9.5 million, the Sox are always willing to overpay in dollars to lessen the number of years. Again, the fact that the deal was for one year only is key.