Here's my shot at it:
1. Keyes didn't "pick" a state to represent. He was invited by the IL GOP.
2. When you say "And I do not mean compromising principles", what does that mean exactly? Maybe if an example were attached to it...
3. I've seen at least a few people on FR say they'd vote for Obama. I remember at least a few people saying they'd vote third party.
4. No, why would there be? But I think his critics' reasons for opposing him are focused far too much on disliking his personality rather than anything really substantial (issues-oriented).
If Keyes were simply a pundit or private person, his words would not be so critical.
He could avoid ceding a single element of his beliefs and still remain more likeable.
I believe he prides himself in his belittling and condescension. Consequently, he will never be elected, IMO.
Because of what I see as flaws that could be overcome with reasonable effort, I question whether or not Keyes wants the victory or just the benefits of the chase.