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SC, your second question first: if an official were to file a lawsuit, the waiver would be interposed as a defense; whether the defense would prevail would be for a jury to determine.
Your first question goes to the matter of proof, the quantum and weight of evidence offered by the official/plaintiff to show where and how he/she contracted the virus. This, again, is for a jury to decide.
Moreover, even if a waiver is deemed valid, the official/plaintiff could argue that the defendant(s) (schools, conferences, assigners, in descending order of potential liability, in my judgment) were grossly negligent, thereby liable despite the waiver.
Waivers are not to be signed or ignored lightly. I will not officiate any school that requires a waiver.
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