The problem with that I see is if the conclave purposely set the dark elves there to stop him in case he chose the darker path, then what would of happened had he chosen not to? He would have died without deserving it since he didn't accept the help.
No. As Fisty said, Raistlin didn't have to ignore the warning someone gave him before he entered the inn, he didn't have to enter that particular inn, and he didn't have to talk with the dark elves, and he definitely didn't have to agree with their plan. He could've followed a different path and faced a different set of challenges. Remember - the Test is designed so that the people they allow to take will be <i>highly likely</i> to pass(barring unforeseen circumstances - such as Fisty).

Could it be said that it was because of what the conclave did to him that he chose to accept it? If so, did the conclave want him to accept it because without it then 5 years down the road he might not have been willing to make the choices and sacrafices he had to in order to dawn the Black Robes and play his part in the defeat of the Dragon Queen?
You overestimate the Conclave.