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Tony is Building+ against Building; his suit is resistant to both cold and electricity which makes tazers, batsuit defense mechanism, liquid nitrogen capsules, the freeze ray and by default makes the tranqs complately useless; the suit is strong enough to rag doll the Batmobile if he gets his hands on it; range advantage with repulsors; and he won't be hacked easily.
Bats on the otherhand easily outskills; has the temporary advantage of Tony thinking he is human level; still has his explosive batarangs; numerous grenades; stealth; deus ex utility belt; trust grappling hook gun; the batmobile with all its missiles and a few lasers; and most importantly, the Batkick.
I was thinking Tony would have a decisive win seeing as he was resistant to almost anything Bats could do, dodge the batmobile attacks and could just play keep away until I remembered a hilarious fact. His suit is not airtight and he doesn't fly with it. You can assume he will but the one time it was used, Tony chose to fight on the ground. After a few minutes of Bruce's guerrilla tactics and most attacks failing, he just gases Tony for GG.
Issue here is that Iron Man not only has a fairly huge AP advantage but the suit not being Airtight won't mean much when it needs to spread around the air.
Also, he flies against Obadiah before realizing Obadiah can fly, so it is not out of character
The Mark V (suitcase suit he used against Whiplash in Monaco) doesn't (or hasn't shown at least) fly. It was only used once and Tony's feet were firmly on the ground.
The comparison with Obadiah makes no sense seeing as Iron Monger is the size of a building. Unless Tony was going to punch at his legs for the fight, yes he had to fly regardless of whether Obie could if he wanted to win.