Even if by some miracle he would win, he'd have negative "coattails" due to the depressed conservative turnout, and would just be rubber-stamping the Democrat agenda anyway.
“....he’s the one candidate Clinton’s negatives wouldn’t stand out so great against.”
You have probably put your finger on the exact reason the media helps him along like they do.....
He most certainly could win a general election. He might not get the R nod, but he could conceivably run as an independent. He would appeal to a majority of voters, that would be the 50-60% of voters that don't vote based on idealogy. They would not be as troubled by his liberal social views. Of course, he may not run, and if Republicans field an electable candidate, so much the better. But don't underestimate Giuliani. Many people who are not conservative have a favorable opinion of him. It sickens me to bring this up, but Bill Clinton was elected twice, with similar views. And I could stomach Giuliani way more than Bubba, even though most Freepers can't.