This lower experience pilot embarked in challenging pre winter conditions, perhaps not familiar to him, as he was from the southern US. He'd filled tho plane with people, and for the length of the planned flight would have had a good load of fuel too. Depending upon the specifics of that plane, it could do it, but it would have been heavy. It was a dark night, with scattered low cloud under a solid ceiling, considerable wind, and possible freezing precipitation, so a challenge for any VFR pilot.
I was a passenger on a Dash 8 in that area at that time, and remember thinking to myself, "not a night for a cross country flight" as we descended into Toronto. I like to think that had I crossed paths with this pilot before his flight, I would have quietly offered some mentoring - like "perhaps this is not the time to depart". I'll remind myself next time that some mentoring could save lives...