I'd have to ask the relevance of this. I know plenty of
tradesmen, like plumbers and electricians, who make pretty decent
money, so what, exactly, is the inherent disadvantage of not being
a profgessional?
Two things. If you recall your secondary school history lessons,
Singapore's geographical position makes it an ideal port - that's
why the British colonised it in the first place. Second, shipping
is but one of many industries, and while I acknowledge Singapore's
advantage in this area, it is not the be-all-and-end-all of
industry and business, so to base a blanket conclusion on this one
point is ill-advised.
So are you saying that if you stay put, you won't have to worry
about the future? If anything, the unemployment system in Australia
and other countries provides more of a safety net than in
Singapore. In Singapore, if you're out of a job and down on your
luck, sorry, you're on your own.
Also, how do you plan for the unforseeable? It is, after all,
called unforseeable for a good reason. 
Again, how is Singapore different? If you have evidence that
retirees are better off in Singapore than in other countries, I'd
be interested in hearing about it.
This one's begging to be asked - have you tried competing in a
non-Singaporean market? On what basis are you forming your
opinions?
Don't take this the wrong way, but I can't see enough of a
foundation and a knowledge base for you to be dispensing advice,
well-intentioned as I assume it to be. I'm quite happily at the top
of my game in Melbourne, and knowing fymk personally, I know she's
doing well too. As you've said, if you have the right attitude,
you'll do well anywhere. Conversely, if you have the wrong
attitude, you won't do well anywhere, and if there's any advantage
to be drawn from not cutting one's roots, it would be for such
people to fall back upon familial support.