Thanks for the advice, Rob. I keep following this story and the details not just because he was a coworker, but because I want to know how it could have been different.
From what I heard, the Sheriff said that he went wide on the first curve and got into some gravel, and apparently overcorrected and went back across the road heading into the next curve, lowsided and then went off and hit the tree. Hard to imagine how fast he must have been going on a 250 for that to happen, but he was at the back of the group and there apparently was no sweeper... so most likely your speculation is on target.
An experienced coworker of mine told me, after talking about this accident, "never ride at more than 50-70% of your ability on the street". Makes sense, save the "pushing the envelope" for the track, where you know the turns, the surface is clean, and there are no trees, lightpoles, or oncoming traffic in case you fuck up.
2011 Ducati Monster 796