When there is a damage to a plane, renters don't ever pay for the damage, that is what insurance is for. My guess is the deductible made it not worthwhile to file a claim for the minor damage, the deductible on a 600K plane is probably fairly high. Frankly surprised the university doesn't just self insure except for liability. Leath is paying for it because of the bad pr and because he is obviously able to , not because of anything nefarious. It is the right thing for him to do and should end any claims of impropriety.
Steady crosswinds are easy to deal with, gusty cross winds can be very difficult to navigate as your control inputs need to constantly adjust for the gusts.
Downdrafts and micro-bursts take down airliners, they survive them by avoiding them. If there really was a downdraft he is lucky to have survived. May have just been an excuse though.
Leath flying himself to meet donors makes sense from an economic sense in that the university doesn't have to pay a pilot. It doesn't make sense in that it can look like a special privilege, he is a less qualified and experienced pilot than would likely otherwise be flying, and his duties and priorities on the ground can cloud his judgement concerning weather, duty day, etc. There is a reason rich guys and rock stars frequently die in plane crashes.
After this incident, it would be foolish for the University to allow any employee to fly on their own, this is not a big scandal though.