#1260, The Hondas with high-skill level. Any car with high skill-level. Again, the cars don't matter, it's if you've raced enough to "buy" more "skill".
#1266, As much as it takes. I don't think I have the patience to get more than about $50k, though.
I'm torn between getting a 92-95 911 Turbo or a Cobra R.