So I really suck at this game, but somehow have managed to get to the decision part about Dimitri. My question is, which story path is easier? I know that whatever you pick affects the next missions and want the smoothest sailing, so any help is appreciated.
It all depends on the helicopter jump at the end. I think if you kill Dimitiri(don't do the deal) there is a ramp you hit in a boat to get to Jacob's copter. Do the deal, and you have to use and the boat and floor it and simply get to the boat. I find this part without the ramp is frustrating.
Go with killing Dimitri instead.
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In both endings you kill Dimitri. In revenge you're going to kill him for what he did to you in the past. Pegorino gets mad at you, and I won't spoil anymore.
In deal, you're going to work for him once more, but he betrays you again. However you manage to complete the job, but then Dimitri sends an assassin to kill Niko which accidentally kills Roman. This way Dimitri becomes the final boss.
So what Master_Smidge says is wrong, in both endings you kill Dimitri. It's wheter you take the initiaive to do it, or he makes you get mad at him again to do it.