Fuck 2 strokes. Look for a 2003 or newer 250 4 stroke. (YZF, RMZ, KXF, CRF) Not a lot of maintenance, plenty of power at any RPM, and easy to ride in alomst all conditions.
Well, I just talked to him, his front end washed out on gravel. He broke a couple ribs, collapsed a lung, and did some damage to his spleen. Was in the hospital for a few days but is ok now.