The 99 year lease, be it for private properties or HDB flats, would morph into a snow man when the time comes. When the lease expires or about to expire, someone who owns a 2 rm or 3rm flat with a balance of 50 year or 70 year lease would be richer than one owning a 5 rm flat or executive flat or even a private property with a 5 year lease or lesser. For at the end of the lease, the value of the no life lease property technically becomes 0. The land plus the property would go back to the owner of the land.
What this means is that 99 year leasehold owners are sitting on a time bomb, a vanishing asset. SG100 will see many properties go up in smokes and the rich owners, if their sole asset is the 99 year leasehold property that is slipping from their grips, be it $3m or $1m, will go pooh pooh.
Maybe this is a good thing, when wealth of one generation will not be passed down to the third generation to continue to be wealthy without having to work, just living on the value of a piece of appreciating property. The diminishing lease and value of 99 year leasehold properties will be like a reset every 2 or 3 generation. And that will be a time when 2 or 3 roomers still with a substantial lease remaining, will become richer than those whose lease expired. They would be looking at the new poor neighbours whose private properties or big HDB flats just become no more, homeless.
SG100 will be a time of reckoning, when the poor becomes rich and rich becomes poor. Things will turn upside down.
Good system for the average Singaporeans. Only those with freehold properties and not subject to estate duties will be rich forever and live happily ever after. The rich have it all thought out, the system will protect them and their wealth for generations to come.