I'd say possibly none of the above; or maybe a combination of all three of them. I think it's simply a hard case with some tough choices, given that his "contract" is an amalgam of the CBA and his own separate agreement with the University, and the two don't always dovetail nicely and cleanly.
As you know, I read the documents to provide the option not to go to arbitration at all, but to go to court instead, which I would have done here because it would have allowed all potential claims to be brought in the same proceeding (and I'm generally not a fan of arbitration anyway). By opting to stay in arbitration, Ollie arguably waives any other claims; and now if he pursues other claims he gives the University the right to pull the plug on the arbitration.
I still think that the most potentially promising claim is breach of the covenant of good faith and fair dealing, and it's not clear to me that they can even bring that claim now that they have chosen to stay in arbitration. As for the CHRO/EEOC claims, as I said when they filed this, I don't think the federal court can even do what they are asking to do, i.e., forgive them for missing a filing deadline for claims that they haven't filed. I think they should have either filed those claims timely in order to preserve them (even though they would have risked having the University pull the plug on the arbitration) or not filed them at all, effectively waiving them. The approach they settled on is like trying to be a little bit pregnant.