As much of a Fett man I am, I'll have to give it to Iron Man. I'm no comics junkie, so I mostly go off of what I see in the Iron Man movies, but come on...a completely armored suit that can travel up to what, Mach 3 for extended periods of time (hours I assume, gotta be a long trip from his pad in Malibu to the Middle East)? Multiple weapons systems, auto targeting, a freaking hand laser in Iron Man 2 that completely destroys anything in its path, even if its got a one use per cartidge deal(possible match for a lightsaber maybe?). Boba Fett has a set of dentable helmet and armor worn over a cloth flightsuit (which supposedly has its own shield...I don't buy that hokey ****, I feel like the authors in the star wars characters books just put a bunch of random "oooohh, that sounds cool" features to anything they could label).
Boba Fett has a flight system all right...that gives him a WHOPPING 1 minutes and 30 seconds of flight time on a full tank. He has a rifle (carbine I'll call it) that requires aiming (rangefinder, in-visor HUD targeting, whatever), and is that going to have the range of an aerial bombardment courtesy of Stark's weapons?. Boba doesn't have a chance.
Now to delve into more nerdy "what-ifs", we'll talk about actual "fighting". Even though Boba Fett probably has the battle and combat expertise of that of someone in CAG (Combat Applications Group, a.k.a. "Delta Force"), I don't think Tony would be at a severe disadvantage. He's received hand to hand combat training, and has done his fair share of "fighting" to gain experience.
I know this probably puts me on the very unpopular side of the argument
, but I have to go with what I see as realistic vs. something insanely cool looking.
Boba Fett will forever be my favorite fictional character, period...But even though you're absolutely awesome, you're not necessarily the strongest.
Plus, if Boba's "man-shield" can't stop an accidental whack from a staff *cough* Han Solo FTW *cough* that sends your "ridiculously advanced flight system" into a tospy turvy malfunction of impending doom, what makes you think it would work from a blast of searing hand-laser?