we do believe that kip is capable of running his gun times. Its the net times which are impossible. I think this is part of the answer.
Kip can do a 20:xx 5k and he may be a 2:59 guy but not a 17:17 and 2:52 guy. He is greedy.
Who are "we"? Most of us do not have reason to believe the notion that he is capable of running the gun times.
As to the delayed start, the most likely scenario is that he can blend in better and nobody will notice him mixed in with several hundred or thousand hobby joggers. Then he can easily hop off the course (perhaps walk off), get in a bike or car and go to the next checkpoint, blend in again and repeat several times.