He thought that Pegula was going to want to bring his own guys in for GM/HC...plus Whaley was just named GM so even if the Pegulas wanted to keep Whaley, there was a chance he'd want to hire "his guy" as HC. From the perspective of late 2014 it makes sense...in retrospect it might not have made any sense.
Hard to know since Whaley wasn't a great GM and he might have ended up going down with Whaley's ship anyway.
Certainly possible. But to take the buyout without another job lined up already seems short sided IMO. If nothing else, make them buy you out after another year or so, and hopefully do well and earn an extenion.