I love Nagy as a coach. He's such an invaluable asset to a young QB with his modern thinking and inventive offensive schemes. Trubisky as a player is as solid as they come. That playoff game made me tip my hat. Kid is tough. That tandem should be successful for the next decade or so. Need to fill out the skill positions around Trubisky.
To answer the question posed though, if we are going with a perfect world with no peripheral injuries then I believe Deshaun Watson would have a better year because of his surrounding cast. Houston may have the best group of WRs in the entire NFL. Chicago in a head scratcher gave up on Jordan Howard for David Montgomery and TArik Cohen? Not sure those guys cant pound it all year, but we'll see. I still like the balance that running Lamar Miller into a wall 20 times a game brings. So far in camp the TEs have looked great in the pass game, if OBrien could find a way to actually integrate tha part of the game (TEs have been virtually nonexistent in the passing game for 2 years in a row now) then it would really be a lethal offensive unit. OL play is crazy suspect, but what we have in Deshaun is that escapability aspect that Trubisky; while very mobile in his own right; seems to have the edge and use as 6th sense.
Hard to ask fanbases of these teams to pick which guy since there will always be a level of bias and favoritism. May be cool to ask a neutral fanbase how they see the comparison.