Singapore has one of the lowest home ownership. The trick in making the leasee pay for exhorbitant prices for a rental flat and take care of the rental apartment is to instill the false notion that the leasee own the apartment. Be it HDB, condo, landed. You are a leasee holding a triple net lease which will eventually depreciate down to zero. No need to wait until 99 years. Give it 40 - 60 years, everything will be falling apart and the remaining value in the lease depreciate even faster. Have you ever been into a building that is >40 or 60 years old? You get the picture. As if that isn't enough, the rules and regulations are there to deter a prospective "buyer" (or perhaps a new leasee would be more appropriate) from taking over the remaining lease with huge upfront and much lower LTV from the bank.
Thinking about sub renting out your whole unit? You sure you making money or working (working as in finding tenants, signing contract, collecting rents, etc..) for free? When one factor in lease decay, PV, FV, it's all an illusion that the any rental money (in real terms) derived from that unit is going into your pocket.
I could be wrong, anyone want to dispute that?