Hi Jeff - that damn radar gets me some times, even though I say I'm not going to pay any attention to it. I went to the first 101 Lakes ride and the sags really sucked then too. I thought they would have sorted that out by now. For $35 entry fee, and with the many, many sponsors that the ride has you would think they would have better sags. I guess I won't bother with them next year either.
I really don't have any answers to your questions about your various scenarios, who is covered, who is not. Ernie provides all the answers at the club meetings, yet questions continue. Like whether or not I would have been covered when I took my detour. The answer is probably no. Yet, when the group goes on its own detour, off the approved map, I'll bet you dollars to donuts that they would be covered. I guess the best advice is just to be "In With The In Crowd".
I'm just going to ride my bike, hope for the best, and ignore the rest