Apple is pretty good at taming technological complexity. The functionality the parent's suggesting could be incorporated into Airport and/or MacOS. Going further, even DynDNS-type services could be something that Apple offers. None of this is to say that there's any economic incentive for them to do it, or that the feature/service would have mass adoption, just that Apple could do it, if they wanted to.

On a long enough curve, nearly every user becomes a "power user," and if you look back, a lot of stuff that was once strictly "advanced configuration," becomes simplified, or eventually just abstracted away and the domain of mere IT mortals. Apple and others could play a role here.

I think you're being naive about how it can be dealt with, technically, by those responsible for pushing OS features forward. But I remain convinced that we'll see robust, decent peer-to-peer system services being integrated into our OS's in the near future, rendering the Cloud impotent in the battle for peoples data.