If the lease gets renewed at market value then there's no point in speculating about what that land might be worth in the farther future. It's a key difference from a system where all of the future value must be captured at once by a single owner.

Doesn't that just turn into a property tax of 1% per year, without a massive tax bill every 99 years? 99 years is long enough that there's going to be at least 2 owners, which means all sorts of strategizing required on how to plan for the renewal of the lease.

Yes, 30 year leases or so would be probably be better. Our Gahmen in Singapore already switched to these shorter leases for commercial property.

The overwhelming majority of homes in Singapore are HDB flats built by the government. These are torn down and new, taller buildings fitting more people built in their place. It's called the Selective En-Block Redevelopment Scheme, or SERS[1]. People sell their flats to the government and are given new flats in other neighbourhoods, while their old homes are torn down and new ones rebuilt. So, yes, in some way, they are 'kicked out'.

[1]: https://www.hdb.gov.sg/residential/living-in-an-hdb-flat/ser...