>This building could easily be half for artists use on the middle floors, a jazz club on the ground floor, and upper section for boutique tech or business HQ offices, maybe a wedding venue on a floor or even a small artsy pre-K school for kids. And the rooftop could have a beautiful green space with a day coffee shop/lounge for nighttime use.

What you're describing would be a complete renovation of the building where you gut and rebuild the entire interior, on top of the cost to buy it along with navigating the complexities of heavy renovation of a landmark status building.

Not sure anything that would require hundreds of millions of dollars in upfront costs could be described as "easily" done.

Also, anyone spending that kind of $$$ would want a ROI. I don't think the artists who could actually afford a space in Flatiron 2.0 are the type you have in mind.

And as far as office space, if a startup wanted Manhattan office space, they could do a lot cheaper than whatever it would cost to rent out space in a newly renovated Flatiron Building.