Do you think you can realistically retire in Singapore without owning property?

Yes

Yes.

No

From own experience of 10 yrs renting in Singapore and finally buy own apartment last year, the law in Singapore does not protect tenant at all. SG landlords/LL can kick you out simply by saying they need it back. Then LL (and their agents) ensure they take most or all of your deposit plus more for fair wear and tear (in commercial property standard lease agreement fair wear and tear is not tenant responsibility) in home rental there is no standard lease agreement and the wording is very ambiguous so that LL could have absolute right and power . LL also has the power to increase rent very high. i had experience where LL give 3 months notice to increase rent by almost 50%! So if you keep renting, anytime you can be homeless and not able to get your deposit back. In other first world country there is law that protect both tenant's rights and LL rights equally since the deposit is in a trust account where landlord cannot touch it until end of lease . Whilst in SG, deposit either directly goes to LL pocket or property agent as part of the commission upfront. Either way, deposit money is gone and it's very hard for tenant to get it back. In addition it is cheaper to pay mortgage (due to low interest rate below 3% for the last 10 yrs) than paying rent . at the end of paying monthly home loan , you get the asset (property) whilst paying monthly rent get you zero asset no matter how long you have been paying rent (which is more expensive than paying home loan).