Is there a site we can legally use to register that bet? I'd be interested in taking it.
I honestly don't think that the headphone jack will ever go away. Wireless audio is like wireless internet, in that it's better than nothing but worse than something with wires and a stable connexion.
I daresay you're correct that Apple think they're right, but … I think they're wrong. The question is, can they remain irrational longer than the rest of the market can be rational? I _think_, given Android's market success, that they ultimately can't: Apple have made too many mistakes in too short a timespan.
But only time will tell.