This is really great on the whole to think about, and the speculation of Apple makes it even better.
Three things that are nitpicky:
1. I like Chase Tower as it is. I feel like in 20 years this will look outdated, while the original tower will become "vintage" (it already kind of is) and stand the test of time (I'm just referring to the exterior look, obviously the inside and the entire base needs work). Just look at the "modernization" that occurred on various original historic buildings through the years and how crappy they are now, while how amazing it would be to just have the original building. e.g. 1 N. 1st Street.
2. If it's fairly real with a larger presence of Apple leasing within the building, not just an Apple store on the ground floor... why not have an Apple logo on top of the building? Imagine that, if that came to fruition. Since the rendering didn't have that, I tend to think it's much less realistic. And the chance a simple Apple store just opens up downtown, here, seems slim to none. If the rendering somehow did include a building-top Apple logo, I'd really be intrigued that this is slightly plausible.
3. The residential tower seems like an uber-fantasy. Or at least a concept without much thought. I don't know much about parking garage structures, other than watching them built through the years via this forum, but it doesn't seem like you can just cut out a quarter of a garage and build a new building in its place. They have ramps and grades/slopes and circulation patterns, it seems impossible to just re-route everything and have it still work. I would think a total tear down and rebuild is the only possible way and maybe more cost-effective.