Interesting theory.
My own view on Guiliani's failure actually mostly has to do with his "brand" faltering against substance than even my own cited biographical/social issues. The less you know about Guiliani, the more you like him. That doesn't really favor a long campaign, let alone "I'm going to win the seventh state filled with New Yor's elderly population" either...
Guiliani was never that much of a candidate for his personal issues to emerge, but I don't think he's particularly relatable to suburban married types.
And this is coming from someone who finds Guiliani mildly appealing..
He might have turned off a lot of people with his personal life, but it seemed like no one cared about Obama's dealings this cycle. The media wouldn't have been Giuliani's ally though.
I do think things might have been different for Rudy if Hillary had won Iowa. He may have performed well in New Hampshire as a result. It seemed that he really just tanked after his health scare in December as well. I really don't know. His campaign will always be a mystery to me. He raised the most money and seemed to have the most "national" campaign of any Republican in 2007. Even a lot of Democrats I knew in the Charleston area had sent him money. But Obama probably took those voters away from him once he won Iowa, and then he collapsed after that.
