What you say has merit. Recently I was having a whiskey soda at the SCC with some old friends. Many have in times past lamented the quality of life in Singapore and have the "grass is greener" mentality. Many have sworn life is indeed better elsewhere and virtually all have a relative who has migrated to NZ or Australia. This conversation was especially interesting as one friend has retired and has declared Australia unfit for retirement. His opinion on the matter was that even if a Singaporean were to say take One million S$ to Australia and pursue retirement there not only is this figure insufficient ;it would result in being delegated as a middle class immigrant.
To explain: One Million S$ is now worth approx AUD$ 700K. With this amount your options are limited to purchase that "big landed property" all Singaporeans covet. If you find one then what? According to this friend you need at least AUD$50-70,000 depending on your lifestyle there to live a quality life comparable to Singapore, so an additional One million S$ would be required to live there comfortably for ten years. Total : 2 Million S$. Its a figure that would make anyone reconsider such a possibility.
What is remarkable was this same conversation several years ago focused on how a Singaporean could take One Million S$ and live the good life playing Golf, free from government intervention, LKY, etc. Another interesting thing to note was these days I am hearing less complaints about life in Singapore as we all consider the alternatives. I think Singapore has changed as it becomes more cosmopolitan.
I have concluded that as far as Australia is concerned the grass is not greener for someone like myself who has assets but not the energy or desire to work hard and pay the high costs associated with a dynamic economic environment. Its a zero sum game.