Interesting question! My take is that Bob is quite well off, has been for some time, and will be able to live out the rest of his days in comfort. I don't see him retiring anytime soon because his position at KSSN is more than a job. He enjoys what he does--something not everyone can say in Modern America. In addition, his audience LOVES him (so do I) and he feels this every day.
Sadly, choosing his replacement will probably be out of KSSN's hands, left up to the bean counters at the New Clear (Nu Clear) Channel. I predict a syndicated replacement when the time comes. To CC, it's all glories to the bottom line, online over on-air.