I don't see Jordan bothering with a "free dinner redemption" unless it's a six figure charity auction. No way on a sportscard redemption. I definitely don't see Topps convincing Brady to Skype with anyone.
I know your examples may have been a tad extreme, but I just don't see the athletes caring enough about the hobby to elevate their committment any further than it is. I really don't see them wanting to help us out when it comes to quality control on a card either.
We'll have to see something "fresh" and "unique" sooner or later. Anyone's guess on what that could be, but few high caliber athletes would be willing to increase their time commitments to the hobby, IMO. We'd end up getting a slew of "Tebow, motivational speech redemptions" and "TO, I need money, so what's for dinner? You're paying, right?" redemptions.