I figured it could be interesting. Hal regularly used to box and spar with both Ollie and Roy and Tony has training from Cap, though it's possible his experience in H2H wasn't as frequent as it was with Hal.
Not really. Extremis and all. Though you could consider it "the suit" for all intents and purposes. For the purpose of this thread though, he's just a normal human without the benefits of Extremis, but not near death or physically ill, either.
Yes. Green Lantern vs. Iron Man has been done (and it's pretty one sided as is, anyway) but both men have shown the ability to handle themselves with nothing but their bare hands.
Hal jordan for the solid majority. Tony has had trouble with a group of kids in the past. I'm a big tony fan, but I know he won't do well in these types of situations. In addition IIRC his training with Cap was just one day. Not encouraging.