I didn't drill my friend for case numbers and rule numbers... However, no many how many "what-ifs" I threw at him (in response to all the variations thrown out here), his reply was the same, windward gets tossed.
I think the only way leeward gets in trouble is if there's contact that causes damage. And windward would still get tossed.
I agree that in the majority (probably vast majority) of such passing situations, if W(indward) cannot keep clear of L(eeward), it is her own fault for getting too close. However, a blanket statement that no matter what "windward gets tossed" is an oversimplification. You can't just ignore rule 16.1. I refer you again to ISAF Case 60.
Sincerely,
Eric
