I actually really like this interpretation of retrofuturism and I think it does a way better job at being respectful to the pedestrian realm than any of the cantilevered examples everyone's pointed out thus far. All of them have set-back bases that create these vacuous street spaces rather than designing a place you want to be in.
I'd be okay if they preserved/restored the Payless building at the corner, if only to break up the facade of the podium. Speaking realistically, this probably isn't in the cards. Also, the Jewelers Building next door has a longer, unbroken facade along Washington Street than this building - the fight over keeping the Payless building is a fight I'm willing to lose if it means we can get rid of that stupid car port.
I like the massing, but I'll agree with those who think the facade makes it look dated, though I don't particularly hate Lake Point Tower - in my layperson's opinion, I think it holds up pretty well. I experienced it in person recently and the worst part was the sheer blank podium at street level (and the dated facade materials).
Keep it curvy - anything to keep the building from deflecting more high altitude winds down to street level.