Judging from Steve Job's final advice to Obama -- "that the administration needed to be more business-friendly", that "regulations and unnecessary costs" make it difficult to build factories in the United States and, crucially, that "until the teachers' unions were broken, there was almost no hope for education reform" -- his personal opinions were far more at home on the WSJ op-ed page, than that of the NY Times.
On the other hand, Apple customers are understood to be predominately Democratic. This is, in part, due to -- as Jobs critiqued -- Microsoft and Google being "pure technology" companies that "never had the humanities and the liberal arts in the DNA". While techies may love their gadgets infinitely customize-able, non-geeks can be confused, or even scared, by over-configure-ability, and, so, prefer technology that works simply. In other words, Apple's appeal lay, largely, in enabling -- for a premium -- the tech-phobic to pose as tech-savvy. One frequent implicit claim of this blog, is that there is an direct analogy in this to the appeal of Democratic politics.
On a darker note, there is more then a touch of nihilism, in the sense of beauty mixed with cruelty, surrounding Jobs, his products and, perhaps, his customers.