no prep, im has a better chance, but still loses. dr.doom 6-7/10.
with prep, dr. doom takes it 9-10/10. dr.doom plotting skills>>im's plotting skills.
and the last one with prep and their respective bots, i'd say tony ends up destroying most of the bots, and most of his suits survive, but dr. doom eventually tricks stark into believing he has defeated doom, only to discover that doom has trapped him or depowered his suit or done somthing that will lead to tony's demise... and the subsequent demise of all his suits as well.