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2 scenerios

1- Tony is at Stark towers Mister Terrific has to get to a computer terminal in the center of the tower to download a program. Tony is trying to guard it. Can Mister Terrific get past him, and his security and hack his systems and get the program. Both have 24 hrs prep, full resources (minus superpowered friends) and basic knowledge of their opposition.

2- Same as above but Mister Terrific in full command of his checkmate headquarters and Tony is trying to get past him and get the program.

Can either or both get to the program or is their opposition just to much.

Tony would have to rely on his own eyes to detect Holt as he's invisible to technology. Considering that Bleeding Edge/Extremis+ is a part of his actual body and gives him enhanced sight, it raises the question if Terrific would be invisible to Tony even without fully manifesting the armor as his body now qualifies as "tech".

Terrific might be able to get past Tony (24 hours isn't a lot of time to overcome Terrific's tech-invisibility, especially when Terrific can counter-prep) but I really don't see him successfully hacking any Stark Towers computer and downloading anything without Tony locating and shutting him down.

Tony on the other hand has better odds of success for infiltrating Checkmate and getting whatever he needs. He's got a LOT of previous armors to pull on for prep, and he's already starting with a significant technopathy advantage.

I'd give odds to Ironman in both scenarios.