The people that have owned for the past 30-50 years, are completely unwilling to give up on their single family homes, gardens, etc. They basically demand to live a nice and cushy suburban life, in the middle of a big city.
It then takes forever to build vertically, because for every projects that's proposed, there are hundreds, of not thousands of protests from neighbors that'll lose some sunlight, depreciation of property value, and what not - or they just don't like the modern architecture. So it can take YEARS to just get the first shovel in ground, because these projects go through so many rounds in city councils and what not.
That's how you end up with extremely partisan / one-sided city councils, consisting of established home/land owners, that will fight tooth and nail to impose draconian zoning laws, and general NIMBY-politics.