This whole concept of loss of potential earnings is complicated, and while Kyle's appeal most certainly will not mention it directly, it has to hang over this decision by the NCAA like a specter.
The NCAA supposedly represents the common interests of its members, and if a decision it makes opens up OSU or Day to a plausible legal liability (and therefore sets a dangerous and costly precedent), it will be extremely cautious with how it proceeds - and is likely getting heavy legal help/advice.
I think historical precedent in similar cases is irrelevant. The age of NIL is here, and a change so profound was bound to have unpredictable and unintended consequences.
That all being said, I don't think a tortious interference claim would succeed - primarily because OSU and Day certainly did not have the intent to block Kyle from something that didn't even exist at the time. But - that is a matter of fact-finding - not legal theory. This 'issue' will only exist for a relatively short window of time (those in school during the NIL transition) - and I can definitely see the NCAA grandfathering waivers during this time just to avoid this ever making it to litigation. Hell - maybe they give Kyle his waiver and ask him to sign one at the same time.